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

HRID 1371470Notes

Reaction equation

HRID 1371470 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25](I)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.[CH:29]([C:31]1[O:32][C:33](B(O)O)=[CH:34][CH:35]=1)=[O:30].COCCOC.CO>[Pd].C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)[NH:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:33]3[O:32][C:31]([CH:29]=[O:30])=[CH:35][CH:34]=3)[CH:26]=2)[N:21]=[CH:20][N:19]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 80711,2-DimethoxyethaneHCID 27343555-Formylfuran-2-boronic acidHCID 101745194-Quinazolinamine, N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-iodo-

Product 1

HCID 11181296(5-(4-(4-((3-Fluorobenzyl)oxy)-3-chloroanilino)-6-quinazolinyl)-2-furancarboxaldehyde

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

To a reaction vessel was added N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-iodo-4-quinazolinamine (100 mg; 0.198 mmol), 2-formylfuran-5-boronic acid (Frontier Scientific, 42 mg; 0.297 mmol), 10% palladium on activated carbon (5 mg; 0.05 wt), DME (2.0 mL), MeOH (1.0 mL) and triethylamine (83 μL). After heating at 50° C. for 14 h, a HPLC indicated 98.5% clean conversion. 1H NMR (d6-DMSO) δ: 11.44 (s, 1H), 9.38 (s, 2H), 9.11 (s, 1H), 8.90 (s, 1H), 8.39 (dd, 1H, J=8 and 4 Hz), 7.89 (d, 1H, J=12 Hz), 7.84 (d, 1H, J=4 Hz), 7.60 (dd, 1H, J=8 and 4 Hz), 7.47–7.42 (m, 2H), 7.44 (AA′BB′, 2H, JAB=8 Hz), 7.35–7.25 (m, 3H), 7.24 (d, 1H, J=4 Hz), 7.16 (dt, 1H, J=8 and 4 Hz), 7.06 (AA′BB′, 2H, JAB=8 Hz, 6.84 (d, 1H, J=4 Hz), 5.27 (s, 2H), 4.43 (s, 2H), 3.61–3.50 (m, 2H), 3.47–3.36 (m, 2H), 3.09 (s, 3H), 2.23 (s, 6H).

Sources & evidence

ORD record
ord-e460c8cec02343ad99651f1a00fbd742
Source dataset
uspto-grants-2007_01
Patent number
US07157466B2

Reaction notes

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