4-Bromo-2-fluorobenzamide → HCID 71114210, compound

HRID 710136Notes

Reaction equation

HRID 710136 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][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[N:14][C:13]=3[CH:30]=2)O1.Br[C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH2:39])=[O:38])=[C:35]([F:42])[CH:34]=1>>[C:37]([C:36]1[CH:40]=[CH:41][C:33]([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][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:21][CH2:22]4)=[N:14][C:13]=3[CH:30]=2)=[CH:34][C:35]=1[F:42])(=[O:38])[NH2:39]

Participants

3

Reactant 2

HCID 27733314-Bromo-2-fluorobenzamideHCID 71090269Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 71114210HCID 71114210, compoundYield 16.3%

Procedure

Following the General Procedure-3, the titled compound (25 mg) was prepared from Intermediate 8 (150 mg, 0.35 mmol) and 4-bromo-2-fluorobenzamide (77 mg, 0.35 mmol) as a white solid. M.P.: 202-206° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.22 (t, J 8.3, 1H), 7.89 (s, 1H), 7.59-7.49 (m, 3H), 7.37 (dd, J 1.6, 13.24, 1H), 6.71 (d, J 9.5, 1H), 5.85 (s, 1H), 4.15 (d, J 10.7, 2H), 3.20-3.10 (m, 1H), 3.00 (t, J 11.8, 2H), 2.20-2.12 (m, 2H), 1.99-1.85 (m, 2H), 1.48 (s, 9H).

Sources & evidence

ORD record
ord-fa77fa573a28434998953bf7b2013efa
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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