4-(Phenylaminocarbonyl)benzeneboronic acid → N-Phenyl-4-[2-(3,4,5-trimethoxy-phenyl)-furo[3,2-b]pyridin-7-yl]-benzamide

HRID 1470381Notes

Reaction equation

HRID 1470381 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[O:10][C:3]=12.[C:23]1([NH:29][C:30]([C:32]2[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:23]1([NH:29][C:30](=[O:31])[C:32]2[CH:37]=[CH:36][C:35]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[C:9]([C:11]5[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=5)[O:10][C:3]=34)=[CH:34][CH:33]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 110967474-(Phenylaminocarbonyl)benzeneboronic acidHCID 667789647-Chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine

Product 1

HCID 66779357N-Phenyl-4-[2-(3,4,5-trimethoxy-phenyl)-furo[3,2-b]pyridin-7-yl]-benzamide

Procedure

The title compound was prepared by procedure C using 7-chloro-2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridine (45.00 mg; 0.14 mmol; 1.00 eq.) instead of 7-chloro-2-iodo-furo[3,2-b]pyridine, and 4-phenylaminocarbonylphenylboronic acid (37.32 mg; 0.15 mmol; 1.10 eq.) instead of 4-fluorophenylboronic acid and was obtained as a yellow solid (68 mg, 100%). (HPLC (method F): 77%, RT: 4.21 min); 1H NMR (500 MHz, DMSO-d6) δ[ppm] 10.41 (s, 1H), 8.65-8.56 (m, 1H), 8.30 (d, J=7.9, 2H), 8.21 (d, J=8.5, 2H), 7.85-7.76 (m, 3H), 7.70 (dd, J=3.9, 1.2, 1H), 7.38 (t, J=7.6, 2H), 7.34 (s, 2H), 7.13 (t, J=7.4, 1H), 3.92 (s, 6H), 3.79-3.70 (m, 3H); MS (m/z) 481 [M+H]+, RT: 4.2 min.

Sources & evidence

ORD record
ord-d3525c8d32d9435abad689dd217fdc4d
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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