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

HRID 1469090Notes

Reaction equation

HRID 1469090 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[CH:21]=[C:22]4[CH:28]=[CH:27][N:26]([Si](C(C)C)(C(C)C)C(C)C)[C:23]4=[N:24][CH:25]=3)[CH:18]=2)[N:13]=[CH:12][N:11]=1.[F-].[Cs+]>C(#N)C>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][N:2]1[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[CH:21]=[C:22]4[CH:28]=[CH:27][NH:26][C:23]4=[N:24][CH:25]=3)[CH:18]=2)[N:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 675137734-(1,3-dihydroisoindol-2-yl)-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline

Product 1

HCID 569666644-(1,3-dihydroisoindol-2-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazolineYield 95.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.12 g of 4-(1,3-dihydroisoindol-2-yl)-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]-pyridin-5-yl)quinazoline and 0.05 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 0.08 g of 4-(1,3-dihydroisoindol-2-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline (“A2”) as white solid (yield 95%, content 96%); MS-FAB (M+H+)=363.8; Rf (polar method): 1.63 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-492fed9de40940538ad86a2b55b5da4e
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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