2-(2-Fluoro-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → Tert-butyl 4-{6-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylate

HRID 710118Notes

Reaction equation

HRID 710118 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([CH:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1.[F:24][C:25]1[CH:30]=[C:29]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:28]=[CH:27][C:26]=1B1OC(C)(C)C(C)(C)O1>>[F:24][C:25]1[CH:30]=[C:29]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:28]=[CH:27][C:26]=1[C:2]1[CH:23]=[CH:22][C:5]2[N:6]=[C:7]([CH:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 682992982-(2-Fluoro-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 71089554Tert-butyl 4-(6-bromobenzo[d]oxazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 71114582Tert-butyl 4-{6-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylateYield 17%

Procedure

Following the General Procedure-1, the titled compound (21 mg) was prepared from Intermediate 10 (100 mg, 0.26 mmol) and Intermediate 3 (102 mg, 0.34 mmol) as an off-white solid. M.P.: 174-178.3° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.85-7.75 (m, 3H), 7.73-7.64 (m, 2H), 7.50 (d, J 8.2, 1H), 4.15 (d, J 12.4, 2H), 3.20-3.10 (m, 4H), 3.0 (t, J 12.5, 2H), 2.20-2.12 (m, 2H), 2.00-1.85 (m, 2H), 1.48 (s, 9H).

Sources & evidence

ORD record
ord-ce7b98fc22ea4cf98661642230d978dd
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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