Methyl iodide → HCID 57980091, compound

HRID 1677188Notes

Reaction equation

HRID 1677188 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:11])[CH:3]=1.[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)(=[O:15])=[O:14].[CH3:25][C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[CH2:31][C@@H:32]1[CH2:36][CH2:35][CH2:34][NH:33]1.[H-].[Na+].IC>>[F:11][C:4]1[CH:3]=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([S:13]([CH3:12])(=[O:15])=[O:14])=[CH:17][CH:18]=2)[CH:10]=[CH:9][C:5]=1[C:6]([N:33]1[CH2:34][CH2:35][CH2:36][C@H:32]1[CH2:31][N:27]1[CH2:28][CH2:29][CH2:30][C@H:26]1[CH3:25])=[O:8]

Participants

6

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3026814-Bromo-2-fluorobenzoic acidHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 46911921(R)-2-methyl-1-((S)-pyrrolidin-2-ylmethyl)pyrrolidine

Product 1

HCID 57980091HCID 57980091, compound

Procedure

The title compound is prepared in a manner substantially analogous to Procedure A′, T′ and B′ starting from 4-bromo-2-fluoro-benzoic acid, 4-methanesulfonylphenyl boronic acid and 2-(R)-Methyl-1-(2-(S)-pyrrolidinylmethyl)pyrrolidine. MS (M+H) 445.2. Alternatively, the title compound maybe prepared by methylation of 3′-fluoro-4-[(2-(R)-methyl-1-(2-(S)-pyrrolidinylmethyl)pyrrolidine-1-carbonyl]-biphenyl-4-sulfinic acid using NaH and iodomethane at 0° C.

Workup

  1. customThe title compound is prepared in a manner substantially analogous to Procedure A′, T′ and B′
  2. customat 0° C.

Sources & evidence

ORD record
ord-6adaf86c013b4ba386a66337836406a2
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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