4-Cyanophenylboronic acid → Tert-butyl 4-[5-(4-cyanophenyl)benzo[d]oxazol-2-yl]piperidine-1-carboxylate

HRID 710122Notes

Reaction equation

HRID 710122 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.[C:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)#[N:25]>>[C:24]([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]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:14][CH2:15]4)=[N:7][C:6]=3[CH:23]=2)=[CH:28][CH:27]=1)#[N:25]

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 71089579Tert-butyl 4-(5-bromobenzo[d]oxazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 71114587Tert-butyl 4-[5-(4-cyanophenyl)benzo[d]oxazol-2-yl]piperidine-1-carboxylateYield 30.1%

Procedure

Following the General Procedure-1, the titled compound (45 mg) was prepared from Intermediate 7 (140 mg, 0.37 mmol) and 4-Cyanophenylboronic acid (53 mg, 0.37 mmol) as an off-white solid. M.P.: 137.3-141.2° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.88 (d, 1.4, 1H), 7.74 (dd, J 1.8, 8.5, 2H), 7.69 (dd, J 1.8, 8.5, 2H), 7.58 (d, J 8.5, 1H), 7.53 (dd, J 1.8, 8.5, 2H), 4.15 (d, J 10.4, 2H), 3.20-3.10 (m, 1H), 3.00 (t, J 11.2, 2H), 2.20-2.12 (m, 2H), 2.00-1.85 (m, 2H), 1.48 (s, 9H).

Sources & evidence

ORD record
ord-a648cfde08744e3886ee53a40a534709
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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