Water → 2-Bromo-7-nitro-5-trityl-pyrrolo[2,3-b]pyrazine

HRID 68663Notes

Reaction equation

HRID 68663 reaction equation
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][N:8]([C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 866757042-bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 866757062-Bromo-7-nitro-5-trityl-pyrrolo[2,3-b]pyrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-bromo-7-nitro-5H-pyrrolo[2,3-b]pyrazine (5 g, 20.57 mmol) was dissolved in DMF (100 mL) under N2. Solution was cooled in an ice bath and sodium hydride (867.1 mg, 22.63 mmol) added portionwise. After 30 minutes (effervescence completed) trityl chloride (6.022 g, 21.60 mmol) was added in one portion and the mixture allowed to warm to ambient temperature (Precipitate observed after around 15 mins). Reaction mixture was poured into water and mixture stirred for 1 hour then filtered. Solid was washed with copious water then dried in a vacuum oven over 48 hours at 80° C. Taken on to the next step as is. (9.7 g, 97.3%) 1H NMR (400.0 MHz, DMSO) δ 8.46 (s, 1H), 8.40 (s, 1H), 7.38-7.36 (m, H), 7.23-7.20 (m, 8H) and 3.32 (s, 7H) ppm

Workup

  1. temperatureSolution was cooled in an ice bath
  2. customReaction mixture
  3. filtrationthen filtered
  4. washSolid was washed with copious water
  5. customthen dried in a vacuum oven over 48 hours at 80° C

Sources & evidence

ORD record
ord-e05f3a61001a413aa89e62427f7b0093
Source dataset
uspto-grants-2014_09
Patent number
US08822469B2

Reaction notes

Loading…