Water → 3,5-Diamino-4-(2-fluoro-5-methyl-pyridin-3-yl)-benzonitrile

HRID 1882229Notes

Reaction equation

[F:1][C:2]1[C:7]([C:8]2[C:15]([N+:16]([O-])=O)=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[N+:19]([O-])=O)=[CH:6][C:5]([CH3:22])=[CH:4][N:3]=1.O>CC(O)=O.[Fe]>[NH2:19][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([NH2:16])[C:8]=1[C:7]1[C:2]([F:1])=[N:3][CH:4]=[C:5]([CH3:22])[CH:6]=1)[C:12]#[N:13]

Participants

Conditions

Temperature: 76 °C

Procedure

Compound 122 (119 mg, 0.39 mmol) was stirred in HOAc (3 mL) with H2O (0.5 mL) and stirred at 76° C. Iron powder (˜325 mesh, 88 mg, 1.56 mmol) was added, and the reaction stirred for 4 h. The solution was concentrated in vacuo, diluted with EtOAc (30 mL), and made basic with sat. NaHCO3. The material was then filtered through Celite, and the organics were separated, dried (MgSO4), and concentrated in vacuo to give 148 mg (66%) of the title compound as a brown oil. MS (ES) [m+H] calc'd for C13H11FN4, 243; found 243.

Workup

stirringthe reaction stirred for 4 h
concentrationThe solution was concentrated in vacuo
additiondiluted with EtOAc (30 mL)
filtrationThe material was then filtered through Celite
customthe organics were separated
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-238bf1dc5e584376b856d1b0f50a27da
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318939B2

Reaction notes

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