HCID 68157720, compound → HCID 68156972, compound

HRID 243157Notes

Reaction equation

HRID 243157 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)[CH:7]=1>[Pd]>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68157720HCID 68157720, compound

Product 1

HCID 68156972HCID 68156972, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(5-Fluoro-2-nitrophenyl)pyrazin-2-yl-amine (415 mg, 1.77 mmol) in IMS (15.0 ml) was added to palladium on charcoal (10 wt %, 45.0 mg) and stirred under a hydrogen atmosphere overnight. The reaction mixture was filtered through Celite® and the filtrate concentrated in vacuo. The product was purified by chromatography (SiO2, 0-10% 2M ammonia methanol/DCM) to yield the title compound (160 mg, 0.78 mmol, 44%). 1H NMR (MeOD, 400 MHz): δ 8.04 (2H, m), 7.83 (1H, m), 7.21 (1H, dd, J 9.9, 2.8 Hz), 6.84 (1H, dd, J 8.7, 5.6 Hz), 6.74 (1H, ddd, J 8.9, 8.2, 2.9 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe product was purified by chromatography (SiO2, 0-10% 2M ammonia methanol/DCM)

Sources & evidence

ORD record
ord-7c2b9f02aba2450aa4b2c52f37a1577d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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