2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester → 4-(6-Hydroxyquinolin-2-yl)-3-methylbenzoic acid

HRID 55804Notes

Reaction equation

HRID 55804 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1B1OC(C)(C)C(C)(C)O1)[C:17]([O:19]C)=[O:18]>>[OH:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([C:23]1[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[CH3:13])[CH:11]=[CH:10]2

Participants

3

Reactant 2

HCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol esterHCID 221325772-Chloroquinolin-6-ol

Product 1

HCID 669800474-(6-Hydroxyquinolin-2-yl)-3-methylbenzoic acid

Procedure

Followed Scheme 3: Starting Materials: 2-chloroquinolin-6-ol and methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate. 1H NMR (DMSO-d6, 400 MHz): δ 10.45 (brs, 1H), 8.61-8.46 (m, 1H), 8.03 (d, J=8.8 Hz, 1H), 7.96 (s, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.66 (d, J=8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 1H), 7.35 (s, 1H), 2.42 (s, 3H). MS (ESI): m/z 279.9 [M+H]+.

Sources & evidence

ORD record
ord-1e450f8fa336456e9f199151c4e059cc
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Reaction notes

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