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

HRID 1469093Notes

Reaction equation

HRID 1469093 reaction equation
[N:1]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]4[CH:22]=[C:23]5[CH:29]=[CH:28][N:27]([Si](C(C)C)(C(C)C)C(C)C)[C:24]5=[N:25][CH:26]=4)[CH:19]=3)[N:14]=[CH:13][N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[F-].[Cs+]>C(#N)C.ClCCl>[N:1]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]4[CH:22]=[C:23]5[CH:29]=[CH:28][NH:27][C:24]5=[N:25][CH:26]=4)[CH:19]=3)[N:14]=[CH:13][N:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 675131214-(3,4-dihydro-2H-quinolin-1-yl)-6-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline

Product 1

HCID 569666654-(3,4-dihydro-2H-quinolin-1-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazolineYield 14.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

0.20 g of 4-(3,4-dihydro-2H-quinolin-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 and 1 ml of dichloromethane 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 0.02 g of 4-(3,4-dihydro-2H-quinolin-1-yl)-6-(1H-pyrrolo[2,3-b]pyridin-5-yl)quinazoline (“A3”) as white solid (yield 13%, content 95%); MS-FAB (M+H+)=377.9; Rf (polar method): 1.79 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-b638a12e4eb647c1912d43aedde93239
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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