Sodium hydride → 2-(2-Bromo-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl)isoindolin-1-one

HRID 627789Notes

Reaction equation

HRID 627789 reaction equation
Br[CH2:2][C:3]1[CH:40]=[CH:39][CH:38]=[CH:37][C:4]=1[C:5]([NH:7][C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([Br:17])[N:15]=2)[N:10]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=1)=[O:6].[H-].[Na+]>CN(C=O)C>[Br:17][C:14]1[N:15]=[C:16]2[C:8]([N:7]3[CH2:2][C:3]4[C:4](=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:5]3=[O:6])=[CH:9][N:10]([C:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:11]2=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 24758Sodium hydride2×HCID 866765052-(bromomethyl)-N-(2-bromo-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl)benzamide

Product 1

HCID 866765062-(2-Bromo-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl)isoindolin-1-oneYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(bromomethyl)-N-(2-bromo-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl)benzamide (1.45 g, 2.223 mmol) dissolved in DMF (20 mL) under N2 and solution cooled in an ice bath. NaH (60% w/w suspension in mineral oil, 89.43 mg, 2.334 mmol) added in two portions and the reaction mixture stirred with cooling. After 2 h, an additional ˜20 mg NaH added. After a further 30 mins, reaction quenched by careful addition of water. The resulting yellow precipitate collected by filtration, washing with water. Precipitate dried at 50° C. in vacuuo to give title compound as a pale yellow solid (1.17 g, 92%); 1H NMR (400 MHz, DMSO) δ 5.37 (2H, s), 7.20-7.22 (5H, m), 7.30-7.39 (10H, m), 7.54 (1H, t), 7.68 (1H, t), 7.74 (1H, d), 7.79 (1H, d), 8.23 (1H, s), 8.59 (1H, s) ppm; MS (ES+) 571.0.

Workup

  1. temperaturesolution cooled in an ice bath
  2. temperaturewith cooling
  3. waitAfter a further 30 mins
  4. customreaction
  5. customquenched by careful addition of water
  6. filtrationThe resulting yellow precipitate collected by filtration
  7. washwashing with water
  8. customPrecipitate dried at 50° C. in vacuuo

Sources & evidence

ORD record
ord-e4bd09a8a71a41a99242c18888d05c22
Source dataset
uspto-grants-2016_04
Patent number
US09309250B2

Reaction notes

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