N-bromobutanimide → Ethyl 6-(bromomethyl)-4-(5-fluoro-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524637Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:22]2[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:26]([CH3:33])[NH:25][C:24]([C:34]3[S:35][CH:36]=[CH:37][N:38]=3)=[N:23]2)=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:9]=2)[CH:7]=1.C1C(=O)N([Br:46])C(=O)C1>>[Br:46][CH2:33][C:26]1[NH:25][C:24]([C:34]2[S:35][CH:36]=[CH:37][N:38]=2)=[N:23][CH:22]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=2[C:8]2[CH:13]=[C:12]([C:14]([F:15])([F:17])[F:16])[CH:11]=[C:10]([C:18]([F:19])([F:21])[F:20])[CH:9]=2)[C:27]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 118107590Ethyl 4-(5-fluoro-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-6-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107610Ethyl 6-(bromomethyl)-4-(5-fluoro-3',5'-bis(trifluoromethyl)-[1,1'-biphenyl]-2-yl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 55%

Procedure

Ethyl 4-(5-fluoro-3′,5′-bis(trifluoromethyl)-[1,1′-biphenyl]-2-yl)-6-methyl-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (5.69 g, 10.2 mmol) was reacted with NBS (2.2 g, 12.2 mmol) according to the procedure as described in Example 1, Step B to give the title compound as a yellow solid (3.57 g, 55%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record: ord-5a46736abeb543fab58dea9f6c81ed4a
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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