2-(Bromomethyl)-1,4-difluorobenzene → HCID 69917404, compound

HRID 1006802Notes

Reaction equation

HRID 1006802 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:33][NH:34][CH2:35][C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[F:43])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:44][C:45]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:46]=1[CH2:47]Br>>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:10][C@H:9]1[CH2:33][N:34]([CH2:47][C:46]1[CH:49]=[C:50]([F:53])[CH:51]=[CH:52][C:45]=1[F:44])[CH2:35][C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[F:43])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 5228302-(Bromomethyl)-1,4-difluorobenzeneHCID 69433288HCID 69433288, compound

Product 1

HCID 69917404HCID 69917404, compound

Procedure

Analogously, (2S,4R)-2-[(2,5-difluoro-benzylamino)-methyl]-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester was treated with 2,5-difluoro-benzylbromide to give (2S,4R)-2-{[bis-(2,5-difluoro-benzyl)-amino]-methyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester which was treated with TFA according to general method B (variation 0° C. to RT) to give (2S,4R)-bis-(2,5-difluoro-benzyl)-(4-tritylsulfanyl-pyrrolidin-2-ylmethyl)-amine yellow oil, MS: 627 (MH+).

Sources & evidence

ORD record
ord-aa7765e167e74cdfb83d0607c39fdc23
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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