Sodium Bicarbonate → HCID 70982085, compound

HRID 62701

Reaction equation

HRID 62701 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 70982085HCID 70982085, compoundYield 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 refluexed 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. waitThe reaction was refluexed 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-9e73964e60ae40439e7e6d594dce469e
Source dataset
uspto-grants-2016_09
Patent number
US09447030B2

Linked notes

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