Thionyl Chloride → 5-chloro-2-(chloromethyl)-7-fluoro-1-(2-(methylsulfonyl)ethyl)-1H-indole

HRID 1500939Notes

Reaction equation

HRID 1500939 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]([CH2:18]O)=[CH:5]2.O=S(Cl)[Cl:22]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[N:7]([CH2:12][CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]([CH2:18][Cl:22])=[CH:5]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 89924003HCID 89924003, compound

Product 1

HCID 899239435-chloro-2-(chloromethyl)-7-fluoro-1-(2-(methylsulfonyl)ethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {5-chloro-7-fluoro-1-[2-(methylsulfonyl)ethyl]-1H-indol-2-yl}methanol (130 mg, 0.43 mmol) in 40 mL of DCM was stirred with SOCl2 (254 mg, 2.13 mmol) at RT and the reaction was monitored by LC/MS. After all starting materials were consumed, the mixture was concentrated in vacuo to afford the crude 5-chloro-2-(chloromethyl)-7-fluoro-1-[2-(methylsulfonyl)ethyl]-1H-indole, which was used for next step directly.

Workup

  1. customAfter all starting materials were consumed
  2. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3c5d63f0ad0c411f89469dc00bef3bed
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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