(3-Methoxyphenyl)boronic acid → HCID 178489665, compound

HRID 1520385Notes

Reaction equation

HRID 1520385 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[N:6]=[C:5]2[OH:18].[O:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)[CH3:20].COC1N=CC(C2C=C3C(=CC=2)N=C(C2C=NC=CC=2)N=C3NC)=CC=1>>[CH3:20][O:19][C:21]1[CH:26]=[C:25]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:6]=[C:5]3[OH:18])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 67298492HCID 67298492, compoundHCID 178517516HCID 178517516, compound

Product 1

HCID 178489665HCID 178489665, compound

Procedure

6-(3-methoxyphenyl)-2-(pyridine-3-yl)quinazoline-4-ol was prepared from 6-bromo-2-(pyridin-3-yl)quinazolin-4-ol (synthesized following Scheme 70 substituting 2-amino-5-bromobenzamide for 2-amino-5-bromo-3-methylbenzamide) and 3-methoxylphenylboronic acid as described in Scheme 72 using method AQ2. The resultant product, 6-(6-methoxypyridin-3-yl)-N-methyl-2-(pyridine-3-yl)quinazoline-4-amine, was a pale yellow solid (19.1 mg, 51%). LCMS m/z=344 (M+1) (Method C) (retention time=2.01 min). 1H NMR (300 MHz, DMSO) δ 9.64 (d, J=1.3 Hz, 1H), 8.84-8.74 (m, 1H), 8.68 (dd, J=6.2, 1.7 Hz, 2H), 8.57 (d, J=1.6 Hz, 2H), 8.16 (ddd, J=14.4, 8.7, 2.2 Hz, 2H), 7.85 (d, J=8.7 Hz, 1H), 7.54 (dd, J=7.9, 4.8 Hz, 1H), 7.00 (d, J=8.7 Hz, 1H), 3.93 (s, 3H), 3.18 (d, J=4.3 Hz, 3H).

Sources & evidence

ORD record
ord-9e4c747542ff4d55b131f959341a1523
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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