Water → HCID 58459146, compound

HRID 2036587Notes

Reaction equation

HRID 2036587 reaction equation
[F:1][C:2]1[CH:7]=C(F)[CH:5]=[CH:4][C:3]=1[N+]([O-])=O.[NH2:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([F:19])[CH:18]=1.CC(C)([O-:23])C.[K+].[OH2:26].C[N:28]([CH:30]=O)C>>[F:19][C:17]1[CH:18]=[C:13]([NH:12][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:30]=2[N+:28]([O-:23])=[O:26])[CH:14]=[N:15][CH:16]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 679672,4-DifluoronitrobenzeneHCID 5744505-Fluoro-3-pyridinamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 58459146HCID 58459146, compound

Procedure

To a solution of 2,4-difluoro-1-nitrobenzene (1.723 mL, 15.71 mmol) and 3-amino-5-fluoropyridine (1.468 g, 13.10 mmol) in DMF (21.83 mL) was added potassium tert-butoxide (2.94 g, 26.2 mmol). The solution was stirred under argon at rt overnight. The solution was poured into water and extracted with EtOAc, organic extracts were dried over magnesium sulfate and concentrated to a brown solid. The brown solid was purified by column chromatography on a silica gel column using 5 to 30% gradient of EtOAc in hexane as eluent to give 5-fluoro-N-(4-fluoro-2-nitrophenyl)pyridin-3-amine as an orange solid: LC-MS (ESI) m/z 252.2 [M+H]+.

Workup

  1. extractionextracted with EtOAc, organic extracts
  2. dry with materialwere dried over magnesium sulfate
  3. concentrationconcentrated to a brown solid
  4. customThe brown solid was purified by column chromatography on a silica gel column

Sources & evidence

ORD record
ord-c8602db58471403382560bc4b53a782a
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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