Trifluoroacetic acid → 3-chloro-6-{1-[4-(cyclopropylsulfanyl)phenyl]-2-[(3R)-pyrrolidin-3-yl]ethenyl}-2-methoxypyridine

HRID 70619Notes

Reaction equation

HRID 70619 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:17]([C:31]2[CH:36]=[CH:35][C:34]([S:37][CH:38]3[CH2:40][CH2:39]3)=[CH:33][CH:32]=2)=[CH:18][C@H:19]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]2)=[N:13][C:14]=1[O:15][CH3:16]>ClCCl>[Cl:8][C:9]1[C:14]([O:15][CH3:16])=[N:13][C:12]([C:17]([C:31]2[CH:32]=[CH:33][C:34]([S:37][CH:38]3[CH2:39][CH2:40]3)=[CH:35][CH:36]=2)=[CH:18][C@H:19]2[CH2:23][CH2:22][NH:21][CH2:20]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67400121tert-butyl (3R)-3-{2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(cyclopropylsulfanyl)phenyl]ethenyl}pyrrolidine-1-carboxylate

Product 1

HCID 673995383-chloro-6-{1-[4-(cyclopropylsulfanyl)phenyl]-2-[(3R)-pyrrolidin-3-yl]ethenyl}-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.5 mL) was added to a solution of tert-butyl (3R)-3-{2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(cyclopropylsulfanyl)phenyl]ethenyl}pyrrolidine-1-carboxylate (EZ mixture) (296 mg) in dichloromethane (3 mL) under ice-cooling, followed by stirring for three hours. The reaction solution was concentrated under reduced pressure to give 3-chloro-6-{1-[4-(cyclopropylsulfanyl)phenyl]-2-[(3R)-pyrrolidin-3-yl]ethenyl}-2-methoxypyridine (EZ mixture) as a crude product (235 mg).

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4f44542ea77f41cda9b076698e676aad
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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