Production Method 1

458-52-6

940298-93-1

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  0 °C; 90 min, 0 °C
1.2 Reagents: Hydrochloric acid ,  Tin dichloride dihydrate Solvents: Water ;  0 °C; 4 h, 0 °C

Reference

Syntheses of 7-fluoro- and 6,7-difluoroserotonin and 7-fluoro- and 6,7-difluoromelatonin

Heredia-Moya, Jorge; Hayakawa, Yoshio; Kirk, Kenneth L., Journal of Fluorine Chemistry, 2006, 127(9), 1256-1260

Production Method 2

801282-00-8

940298-93-1

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid ,  Stannous chloride Solvents: Water ;  0 °C; 24 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  basified, rt

Reference

Identification, Structure-Activity Relationship, and Biological Characterization of 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indoles as a Novel Class of CFTR Potentiators

Brindani, Nicoletta; Gianotti, Ambra; Giovani, Simone; Giacomina, Francesca; Di Fruscia, Paolo; et al, Journal of Medicinal Chemistry, 2020, 63(19), 11169-11194

Production Method 3

940298-93-1

Reaction Conditions

Reference

Preparation of indolylalkyl benzamides as EP2 receptor antagonists

, European Patent Organization, , ,

Production Method 4

458-52-6

940298-93-1

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid ,  Stannous chloride Solvents: Water ;  0 °C; 24 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  basified

Reference

Pyridoindole compounds and compositions for the treatment of cystic fibrosis and their preparation

, World Intellectual Property Organization, , ,

Production Method 5

1567373-55-0

940298-93-1

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Platinum Solvents: Methanol ;  3 d, rt
1.2 Reagents: Acetic acid ,  Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  0 °C; 1.5 h, 0 °C → 60 °C; 60 °C → 0 °C
1.3 Reagents: Hydrochloric acid ,  Stannous chloride Solvents: Water ;  30 min, 0 °C

Reference

Preparation of pyrrolopyrazoles as N-type calcium channel blockers for treating pain

, World Intellectual Property Organization, , ,

Production Method 6

458-52-6

940298-93-1

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrochloric acid Solvents: Water ;  30 min, 0 °C
1.2 Reagents: Hydrochloric acid ,  Stannous chloride Solvents: Water ;  0 °C; 1.5 h, 0 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 10, cooled
1.4 Reagents: Hydrochloric acid Solvents: 1,4-Dioxane ;  acidified

Reference

Preparation of indolylalkyl benzamides as EP2 receptor antagonists

, World Intellectual Property Organization, , ,

Production Method 7

940298-93-1

Reaction Conditions

Reference

Continuous flow synthesis process for phenylhydrazine salt and substituted phenylhydrazine salt

, World Intellectual Property Organization, , ,

(2-Fluoro-4-methoxyphenyl)hydrazine hydrochloride Raw materials

• Benzene, 2-fluoro-4-methoxy-1-nitro-, hydrochloride (1:1)
• 2-Fluoro-4-methoxyaniline
• 2-fluoro-3-methoxy-aniline

(2-Fluoro-4-methoxyphenyl)hydrazine hydrochloride Preparation Products

• (2-Fluoro-4-methoxyphenyl)hydrazine hydrochloride (940298-93-1)

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