Cesium fluoride → 4-(2,3-dihydroindol-1-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline

HRID 1469087Notes

Reaction equation

HRID 1469087 reaction equation
[N:1]1([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:21]=[C:22]5[CH:28]=[CH:27][N:26]([Si](C(C)C)(C(C)C)C(C)C)[C:23]5=[N:24][CH:25]=4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[F-].[Cs+]>C(#N)C>[N:1]1([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:21]=[C:22]5[CH:28]=[CH:27][NH:26][C:23]5=[N:24][CH:25]=4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 675131104-(2,3-dihydroindol-1-yl)-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-quinazoline

Product 1

HCID 569666634-(2,3-dihydroindol-1-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazolineYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.19 g of 4-(2,3-dihydroindol-1-yl)-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]-pyridin-5-yl)quinazoline and 0.08 g of caesium fluoride in 1 ml of acetonitrile are stirred at 25° C. in a flask until the reaction is complete (HPLC check, about 24 hours). A precipitate precipitates out of the reaction solution. This is filtered off, rinsed with water and dried, giving 0.04 g of 4-(2,3-dihydroindol-1-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline as white solid (yield 31%, content 97%); MS-FAB (M+H+)=363.9; Rf (polar method): 1.71 min;

Workup

  1. custom(HPLC check, about 24 hours)
  2. customA precipitate precipitates out of the reaction solution
  3. filtrationThis is filtered off
  4. washrinsed with water
  5. customdried

Sources & evidence

ORD record
ord-6bb945a73ef74e389f95d259605f1980
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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