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

HRID 627786Notes

Reaction equation

HRID 627786 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-c8bc2b1547754b6f8bedd6b52394dae3
Source dataset
uspto-grants-2016_04
Patent number
US09309250B2

Reaction notes

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