Sodium hydride → HCID 136351950, compound

HRID 1392117Notes

Reaction equation

HRID 1392117 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=2)[NH:5]1.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:25][CH:26]=2)[N:21]=[CH:20][N:19]=1>O1CCCC1.CN1CCCC1=O>[OH:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[C:18]1[C:27]3[C:22](=[CH:23][C:24]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:25][CH:26]=3)[N:21]=[CH:20][N:19]=1)=[CH:10][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2773516Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylateHCID 10681434HCID 10681434, compound

Product 1

HCID 136351950HCID 136351950, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

Sodium hydride (58 mg, 1.45 mmol, 60% in oil) was washed with petroleum ether (3×5 mL) and dried in vacuo. The solid was suspended in tetrahydrofuran (3 mL) and methyl 2-oxo-5-indolinecarboxylate (140 mg, 0.73 mmol) in tetrahydrofuran (2 mL) and N-methylpyrrolidinone (2 mL) was added. The reaction mixture was stirred for 30 min at room temperature. A solution of 4-chloro-7-(2-methoxyethoxy)quinazoline (183 mg, 0.77 mmol, described in WO 97/42187) in tetrahydrofuran (2 mL) and N-methylpyrrolidinone (1 mL) was added and the reaction mixture was stirred for 1.5 h at room temperature. The solvent was removed in vacuo and 1 M hydrochloric acid was added. The precipitate formed was filtered off and dried at 40° C. in vacuo over night to give 150 mg (99% yield) of the title compound as an orange solid: MS (AP+) m/z 394.2 (M++1).

Workup

  1. customdried in vacuo
  2. stirringthe reaction mixture was stirred for 1.5 h at room temperature
  3. customThe solvent was removed in vacuo and 1 M hydrochloric acid
  4. additionwas added
  5. customThe precipitate formed
  6. filtrationwas filtered off
  7. customdried at 40° C. in vacuo over night

Sources & evidence

ORD record
ord-320aefd6956e4a0aac7bca80f30f2dc9
Source dataset
uspto-grants-2008_03
Patent number
US07342022B2

Reaction notes

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