(5-Acetylthiophen-2-yl)boronic acid → HCID 68083907, compound

HRID 1470383Notes

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

Participants

Reactant 2

HCID 4143377(5-Acetylthiophen-2-yl)boronic acid

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

Product 1

HCID 68083907HCID 68083907, compound

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 5-acetyl-2-thiopheneboronic acid (26.32 mg; 0.15 mmol; 1.10 eq.) instead of 4-fluorophenylboronic acid and was obtained as a yellow solid (15 mg, 26%). (HPLC (method F): 88%, RT: 3.84 min); 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.56 (d, J=5.1, 1H), 8.22 (d, J=4.0, 1H), 8.12 (d, J=3.8, 1H), 7.79 (d, J=1.0, 1H), 7.78 (d, J=5.1, 1H), 7.40 (s, 2H), 3.94 (s, 6H), 3.76 (d, J=0.9, 3H), 2.63 (s, 3H); MS (m/z) 410 [M+H]+, RT: 2.5 min.

Sources & evidence

ORD record: ord-5d942c7401f74f518259d3d5b6b47ffc
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006440B2

Reaction notes

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