Bromide ion → HCID 67004364, compound

HRID 217146Notes

Reaction equation

HRID 217146 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[C:4]([N+:14]([O-:16])=[O:15])[C:3]=1[NH2:17].[Br-]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:14]([C:4]1[CH:5]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=[C:2]([C:9]2[CH:8]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:3]=1[NH2:17])([O-:16])=[O:15]

Participants

5

Reactant 2

HCID 259Bromide ionHCID 67004539HCID 67004539, compound

Product 1

HCID 67004364HCID 67004364, compoundYield 150.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-6-nitro-4-pyridin-3-yl-phenylamine (100 mg, 1 eq), 2-pyridylznic bromide (6 eq) and tetrakis(triphenylphosphine)palladium (0.1 eq) in THF (10 mL) was heated at 100° C. for 18 hours. The reaction was quenched with water (2 mL). The product was extracted with EtOAc (20×3). The combined organic layer was then concentrated in vacuo and the residue was purified by chromatography (Silica Gel, EtOAC) to afford the title compound (75 mg) as a yellow solid. (M+1) 293.

Workup

  1. customThe reaction was quenched with water (2 mL)
  2. extractionThe product was extracted with EtOAc (20×3)
  3. concentrationThe combined organic layer was then concentrated in vacuo
  4. customthe residue was purified by chromatography (Silica Gel, EtOAC)

Sources & evidence

ORD record
ord-cc68f5c9d3474c4e844d68d1ace7a88d
Source dataset
uspto-grants-2012_06
Patent number
US08193352B2

Reaction notes

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