4-Formylphenylboronic Acid → Isopropyl 4-[5-(4-formylphenyl)benzo[d]oxazol-2-yl]piperidine-1-carboxylate

HRID 710146Notes

Reaction equation

HRID 710146 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][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=[N:7][C:6]=2[CH:22]=1.[CH:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)=[O:24]>>[CH:23]([C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([CH:10]4[CH2:15][CH2:14][N:13]([C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]4)=[N:7][C:6]=3[CH:22]=2)=[CH:27][CH:26]=1)=[O:24]

Participants

3

Reactant 2

HCID 5910734-Formylphenylboronic AcidHCID 71257568Isopropyl 4-(5-bromobenzo[d]oxazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 71475815Isopropyl 4-[5-(4-formylphenyl)benzo[d]oxazol-2-yl]piperidine-1-carboxylateYield 34.9%

Procedure

Following the General Procedure-1, the titled compound (100 mg) was prepared from Intermediate 13 (270 mg, 0.73 mmol) and 4-formylphenylboronic acid (132 mg, 0.88 mmol) as an off-white solid. M.P.: 167-170° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 10.07 (S, 1H), 7.96 (dd, J 1.7, 6.6, 2H), 7.93 (s, 1H), 7.76 (d, J 8.2, 2H), 7.58 (s, 2H), 4.95 (septet, J 6.2, 1H), 4.20 (d, J 11.1, 2H), 3.22-3.13 (m, 1H), 3.04 (t, J 11.3, 2H), 2.18 (dd, J 2.8, 13.3, 2H).

Sources & evidence

ORD record
ord-e16114e93e0c4c6ebce135f3fd1f050e
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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