Cesium carbonate → 4-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-2-(2-fluoro-phenyl)-quinazoline

HRID 2387254Notes

Reaction equation

HRID 2387254 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[N:3]=1.[NH:19]1[C:27]2[CH:26]=[CH:25][N:24]=[CH:23][C:22]=2[CH2:21][CH2:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[N:19]1([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[N:3]=2)[C:27]2[CH:26]=[CH:25][N:24]=[CH:23][C:22]=2[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 47382154-Chloro-2-(2-fluoro-phenyl)-quinazolineHCID 124909791H,2H,3H-pyrrolo(3,2-c)pyridine

Product 1

HCID 184406464-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-2-(2-fluoro-phenyl)-quinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-(2-fluoro-phenyl)-quinazoline from Step C example 1 (0.04 g, 0.15 mmol) was dissolved in N,N-dimethylformamide (0.5 ml) and to it was added 2,3-dihydro-1H-pyrrolo[3,2-c]pyridine (0.02 g, 0.16 mmol) followed by cesium carbonate (0.12 g, 0.36 mmol). The mixture was magnetically stirred at room temperature for 0.5 hr. The solvent was removed and title compound was obtained pure after column purification on a HPLC reverse phase column, using a water and acetonitile gradient containing 0.1% trifluoroacetic acid to yield (0.01 g, 19%). MS (ES) 343.0 (M+H)+

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-75137dbe36834a9e9578383b9cdce43f
Source dataset
uspto-grants-2012_09
Patent number
US08268857B2

Reaction notes

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