Sodium Bicarbonate → N-(2-nitro-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide

HRID 2201708Notes

Reaction equation

HRID 2201708 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][C:5]=1[NH:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21])([O-:3])=[O:2].C(=O)(O)[O-].[Na+].Br[C:33]1[CH:38]=[N:37][CH:36]=[CH:35][N:34]=1>[Pd]>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:33]2[CH:38]=[N:37][CH:36]=[CH:35][N:34]=2)=[CH:6][C:5]=1[NH:19][C:20]([N:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1)=[O:21])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6428002-BromopyrazineHCID 70982655N-(2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine-1-carboxamide

Product 1

HCID 70982085N-(2-nitro-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamideYield 70%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of N-(2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine-1-carboxamide (0.20 g, 0.55 mmol) was added at room temperature sodium bicarbonate (0.09 g, 0.80 mmol, 1.45 equiv.), 2-bromopyrazine (0.14 g, 0.89 mmol, 1.6 equiv.) and palladium (0.07 g, 0.06 mmol, 0.1 equiv). The reaction was refluxed for fourteen hours. The crude reaction was filtered and concentrated. The residue was diluted into water and washed with ethyl acetate, the concentrated. The obtained was purified through column chromatography by eluting ethyl acetate and hexane to allow N-(2-nitro-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide (0.12 g, 70% yield).

Workup

  1. temperatureThe reaction was refluxed for fourteen hours
  2. customThe crude reaction
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. additionThe residue was diluted into water
  6. washwashed with ethyl acetate
  7. customThe obtained was purified through column chromatography
  8. washby eluting ethyl acetate and hexane

Sources & evidence

ORD record
ord-f8e82b0277884cfa82109678588fd5b2
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

Loading…