Di-isopropyl 3-furylboronate → 6-(3-Furyl)-4-[3-methyl-4-(2-pyridylmethoxy)anilino]-quinazoline

HRID 2184683Notes

Reaction equation

HRID 2184683 reaction equation
Cl.Cl.Br[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[C:17]([CH3:29])[CH:16]=1.[O:30]1[CH:34]=[CH:33][C:32](B(OC(C)C)OC(C)C)=[CH:31]1>>[O:30]1[CH:34]=[CH:33][C:32]([C:4]2[CH:5]=[C:6]3[C:11](=[CH:12][CH:13]=2)[N:10]=[CH:9][N:8]=[C:7]3[NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:17]([CH3:29])[CH:16]=2)=[CH:31]1

Participants

3

Reactant 2

HCID 13903463Di-isopropyl 3-furylboronateHCID 224783866-Bromo-4-[3-methyl-4-(2-pyridylmethoxy)anilino]quinazoline dihydrochloride salt

Product 1

HCID 224784256-(3-Furyl)-4-[3-methyl-4-(2-pyridylmethoxy)anilino]-quinazolineYield 55%

Procedure

Using an analogous procedure to that described in Example 5, 6-bromo-4-[3-methyl-4-(2-pyridylmethoxy)anilino]quinazoline dihydrochloride salt was reacted with di-isopropyl 3-furylboronate to give 6-(3-furyl)-4-[3-methyl-4-(2-pyridylmethoxy)anilino]-quinazoline in 55% yield, m.p. 206-208° C.; NMR Spectrum: 2.32 (s, 3H), 5.22 (s, 2H), 7.05 (d, 1H), 7.15 (d, 1H), 7.36 (m, 1H), 7.55 (m, 3H), 7.75 (d, 1H), 7.87 (m, 2H), 8.1 (m, 2H), 8.33 (d, 1H), 8.48 (s, 1H), 8.6 (m, 1H), 8.69 (d, 1H), 9.62 (s, 1H); Elemental Analysis: Found C, 73.2; H, 4.9; N, 13.6; C25H20N4O2 requires C, 73.5; H, 4.9; N, 13.7%.

Sources & evidence

ORD record
ord-f35ed8e9149b4f038c65d2a513d31757
Source dataset
uspto-grants-2002_06
Patent number
US06399602B1

Reaction notes

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