Potassium Carbonate → (5-(4-(4-((3-Fluorobenzyl)oxy)-3-chloroanilino)-6-quinazolinyl)-2-furancarboxaldehyde

HRID 877080Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26](I)[CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1.[O:30]1[CH:34]=[CH:33][CH:32]=[C:31]1B(O)O.[C:38]([O-])([O-])=[O:39].[K+].[K+]>[Pd].CCO.COCCOC>[Cl:2][C:3]1[CH:4]=[C:5]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:34]4[O:30][C:31]([CH:38]=[O:39])=[CH:32][CH:33]=4)[CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of [3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-(6-iodo-quinazolin-4-yl)-amine hydrochloride salt (5.05 g, 10 mmol), 2-furylboronic acid (1.85 g, 12 mmol) and palladium catalyst (730 mg, 1.0 mmol) in 10 mL of K2CO3(2.0M), 10 mL of EtOH and 40 mL of DME was heated at 75° C. under nitrogen atmosphere for 4 hr. LS-MS showed the reaction completed. Concentrated the mixture under reduced pressure and washed the residue with water (2×50 mL) then with cool ether (100 mL) to get a gray solid (4.5 g), which was used for next step without further purification.

Workup

concentrationConcentrated the mixture under reduced pressure
washwashed the residue with water (2×50 mL)

Sources & evidence

ORD record: ord-255313f93ab0470eabb9fc3f6e909dbb
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987284B2

Reaction notes

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