Water → 6-Bromo-2-(2-fluoro-phenyl)-4-pyrrolo[3,2-c]pyridin-1-yl-quinazoline

HRID 457717Notes

Reaction equation

HRID 457717 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[N:6]=[C:5]2Cl.[NH:20]1[C:28]2[CH:27]=[CH:26][N:25]=[CH:24][C:23]=2[CH:22]=[CH:21]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[N:6]=[C:5]2[N:20]1[C:28]2[CH:27]=[CH:26][N:25]=[CH:24][C:23]=2[CH:22]=[CH:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 92205-AzaindoleHCID 10796Cesium carbonateHCID 184406506-Bromo-4-chloro-2-(2-fluorophenyl)quinazoline

Product 1

HCID 103647546-Bromo-2-(2-fluoro-phenyl)-4-pyrrolo[3,2-c]pyridin-1-yl-quinazolineYield 101.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-4-chloro-2-(2-fluoro-phenyl)-quinazoline from Step D (1 g, 2.9 mmol) was dissolved in N,N-dimethyl formamide (3 ml) and to it was added 1H-Pyrrolo[3,2-c]pyridine (0.346 g, 2.9 mmol) followed by cesium carbonate (0.961 g, 2.9 mmol). The mixture was magnetically stirred at room temperature for 1 hr. Water was added and the product filtered to yield title compound (1.236 g, 98%). MS (ES) 420 (M+H)+

Workup

  1. filtrationthe product filtered

Sources & evidence

ORD record
ord-68296ea504de4a36968448d4de8f7e40
Source dataset
uspto-grants-2007_03
Patent number
US07189733B2

Reaction notes

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