Potassium Fluoride → Tert-butyl 4-[2-(4-carbamoyl-3-fluorophenyl)benzo[d]oxazol-5-yl]piperidine-1-carboxylate

HRID 710184Notes

Reaction equation

Br[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[CH:7][C:5]=2[N:6]=1.[F:24][C:25]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[CH:30][C:26]=1[C:27]([NH2:29])=[O:28].[F-].[K+]>CN(C=O)C.O>[C:27]([C:26]1[CH:30]=[CH:31][C:32]([C:2]2[O:3][C:4]3[CH:10]=[CH:9][C:8]([CH:11]4[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]4)=[CH:7][C:5]=3[N:6]=2)=[CH:33][C:25]=1[F:24])(=[O:28])[NH2:29]

Participants

Conditions

Temperature: 90 °C

Procedure

Intermediate 52 (40 mg, 0.1 mmol), 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (30 mg, 0.12 mmol) and KF (18 mg, 0.3 mmol) were dissolved in a mixture of DMF (1 ml) and water (0.4 ml). This mixture was purged with N2 for 30 mins. Pd(dppf)Cl2.CH2Cl2 was added to the above mixture and again purged with N2 for 30 mins. This reaction mixture was heated to 90° C. for 12 h. Work up (EtOAc and H2O) followed by purification on combiflash using a gradient mixture of EtOAc and Petether (55:45) as eluent afforded the titled compound (3 mg) as an Off-White solid. MS (m/z): 439.5 [M+H]+.

Workup

customThis mixture was purged with N2 for 30 mins
additionCH2Cl2 was added to the above mixture
customagain purged with N2 for 30 mins
customfollowed by purification on combiflash
additiona gradient mixture of EtOAc and Petether (55:45) as eluent

Sources & evidence

ORD record: ord-a4e88227929c4baa96da9e58a369b016
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181214B2

Reaction notes

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