4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide → Isopropyl 4-{5-[3-fluoro-4-(2-hydroxyethylcarbamoyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylate

HRID 710163Notes

Reaction equation

HRID 710163 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:43]=[CH:42][C:35]([C:36]([NH:38][CH2:39][CH2:40][OH:41])=[O:37])=[C:34]([F:44])[CH:33]=1>>[F:44][C:34]1[CH:33]=[C:32]([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][CH:26]([CH3:27])[CH3:28])=[O:24])[CH2:19][CH2:18]4)=[N:14][C:13]=3[CH:29]=2)[CH:43]=[CH:42][C:35]=1[C:36](=[O:37])[NH:38][CH2:39][CH2:40][OH:41]

Participants

3

Reactant 2

HCID 433929374-bromo-2-fluoro-N-(2-hydroxyethyl)benzamideHCID 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 71114477Isopropyl 4-{5-[3-fluoro-4-(2-hydroxyethylcarbamoyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylateYield 32.2%

Procedure

Following the General Procedure-3, the titled compound (65 mg) was prepared from Intermediate 14 (200 mg, 0.54 mmol) and 4-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide (110 mg, 0.43 mmol) as a brown solid. M.P.: 145-147° C. MS (m/z): 470.4 [M+H]+

Sources & evidence

ORD record
ord-b1364bb33f454d8fb47021c982eaabfe
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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