2-(2-Fluoro-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → Tert-butyl 4-{7-fluoro-5-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylate

HRID 710121Notes

Reaction equation

HRID 710121 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:24])[C:5]2[O:9][C:8]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=[N:7][C:6]=2[CH:23]=1.[F:25][C:26]1[CH:31]=[C:30]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:29]=[CH:28][C:27]=1B1OC(C)(C)C(C)(C)O1>>[F:24][C:4]1[C:5]2[O:9][C:8]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=[N:7][C:6]=2[CH:23]=[C:2]([C:27]2[CH:28]=[CH:29][C:30]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:31][C:26]=2[F:25])[CH:3]=1

Participants

3

Reactant 2

HCID 682992982-(2-Fluoro-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 71089611Tert-butyl 4-(5-bromo-7-fluorobenzo[d]oxazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 71114586Tert-butyl 4-{7-fluoro-5-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylateYield 20.3%

Procedure

Following the General Procedure-1, the titled compound (50 mg) was prepared from Intermediate 12 (200 mg, 0.50 mmol) and Intermediate 3 (151 mg, 0.50 mmol) as an off-white solid. M.P.: 155.3-158.4° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.82 (dd, J 1.8, 8.1, 1H), 7.78 (dd, J 1.7, 9.4, 1H), 7.69-7.63 (m, 2H), 7.29 (td, 1.3, 10.6, 1H), 4.16 (d, J 11.2, 2 H), 3.22-3.16 (m, 1H), 3.11 (s, 3H), 3.00 (t, J 13.3, 2H), 2.21-2.14 (m, 2H), 2.00-1.88 (m, 2H), 1.48 (s, 9H).

Sources & evidence

ORD record
ord-a90aa4a01fa84c72a19a2a046f1e82a5
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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