4-(Trifluoromethyl)phenylboronic acid → Tert-butyl 4-{5-[4-(trifluoromethyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylate

HRID 710126Notes

Reaction equation

HRID 710126 reaction equation
Br[C:2]1[CH:3]=[CH:4][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:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>>[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([CH:10]4[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15]4)=[N:7][C:6]=3[CH:23]=2)=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 71089579Tert-butyl 4-(5-bromobenzo[d]oxazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 71114195Tert-butyl 4-{5-[4-(trifluoromethyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylateYield 23%

Procedure

Following the General Procedure-1, the titled compound (40 mg) was prepared from Intermediate 7 (150 mg, 0.4 mmol) and 4-(trifluoromethyl)phenylboronic acid (74 mg, 0.39 mmol) as an off-white solid. M.P.: 166-169° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.88 (d, J 1.2, 1H), 7.73-7.67 (m, 4H), 7.59-7.52 (m, 2H), 4.15 (d, J 10, 2H), 3.20-3.10 (m, 1H), 3.00 (t, J 11.6, 2H), 2.21-2.12 (m, 2H), 1.99-1.86 (m, 2H), 1.48 (s, 9H).

Sources & evidence

ORD record
ord-440ca1f92adf44839769640edcdfe35a
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

Loading…