Benzamide, 4-bromo-2-fluoro-N-methyl- → Isopropyl 4-{5-[3-fluoro-4-(methylcarbamoyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylate

HRID 710159Notes

Reaction equation

HRID 710159 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[N:14][C:13]=3[CH:29]=2)O1.Br[C:32]1[CH:41]=[CH:40][C:35]([C:36]([NH:38][CH3:39])=[O:37])=[C:34]([F:42])[CH:33]=1>>[F:42][C:34]1[CH:33]=[C:32]([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH:17]4[CH2:18][CH2:19][N:20]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]4)=[N:14][C:13]=3[CH:29]=2)[CH:41]=[CH:40][C:35]=1[C:36](=[O:37])[NH:38][CH3:39]

Participants

3

Reactant 2

HCID 24694329Benzamide, 4-bromo-2-fluoro-N-methyl-HCID 71090092Isopropyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 71257242Isopropyl 4-{5-[3-fluoro-4-(methylcarbamoyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylateYield 33.7%

Procedure

Following the General Procedure-3, the titled compound (80 mg) was prepared from Intermediate 14 (200 mg, 0.54 mmol) and 4-bromo-2-fluoro-N-methylbenzamide (200 mg, 0.54 mmol) as a brown solid. M.P.: 116-120° C. MS (m/z): 440.3 [M+H]+.

Sources & evidence

ORD record
ord-7b7bc5741db448d99687c7f68a2e2ba4
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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