HCID 86699133, compound → HCID 86699061, compound

HRID 1424220Notes

Reaction equation

HRID 1424220 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:10]([F:16])[CH:9]=2)=[C:4]([Cl:17])[C:3]=1[N+:18]([O-])=O>CC(O)=O.C1COCC1.O.[Zn]>[NH2:18][C:3]1[C:4]([Cl:17])=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[C:10]([F:16])[CH:9]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

6

Reactant 1

HCID 86699133HCID 86699133, compound

Product 1

HCID 86699061HCID 86699061, compoundYield 103.1%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (0° C.) of zinc dust (9.34 g, 143 mmol) in AcOH (33 mL), THF (33 mL) and water (9.5 mL) was added 4′-amino-2′-chloro-3-fluoro-3′-nitrobiphenyl-4-carbonitrile (Preparation 93, 2.6 g, 8.93 mmol) and the reaction was allowed to warm to room temperature for 1 hour before filtering through arbocel. The filtrate was diluted with water (200 mL) and EtOAc (200 mL) and the organic layer was collected, dried over MgSO4 and concentrated in vacuo to afford the title compound (2.41 g, quant).

Workup

  1. filtrationbefore filtering through arbocel
  2. additionThe filtrate was diluted with water (200 mL) and EtOAc (200 mL)
  3. customthe organic layer was collected
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10d48a6d03744c4492e4d7894b002764
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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