Ammonia → HCID 89444902, compound

HRID 526040

Reaction equation

HRID 526040 reaction equation
F[C:2]1[C:7]([N:8]2[CH:12]=[CH:11][CH:10]=[CH:9]2)=[C:6]([CH3:13])[CH:5]=[CH:4][N:3]=1.[NH3:14]>>[CH3:13][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH2:14])[C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 894449772-Fluoro-4-methyl-3-(1H-pyrrol-1-yl)pyridine

Product 1

HCID 89444902HCID 89444902, compoundYield 76%

Conditions

Temperature
150 °C

Procedure

2-Fluoro-4-methyl-3-(1H-pyrrol-1-yl)pyridine (3.9 g, 22.1 mmol) was dissolved in 80 mL of ammonia solution (7N in MeOH) in a sealed tube (350 mL). The mixture was heated at 150° C. for 2 days protected with a blast shield. The mixture was cooled to room temperature, then cooled in the ice for minutes. The filtrate was evaporated to dryness and purified by flash chromatography (EtOAc/Hexanes=1:1, Rf=0.5) to give 2.9 g (76%) white solid. 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J=5.1 Hz, 1H) 6.67 (t, J=2.1 Hz, 2H), 6.60 (d, J=5.2 Hz, 1H), 6.41 (t, J=2.1 Hz, 2H), 4.52 (s, 2H), 2.02 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 156.1, 147.2, 145.9, 121.5, 121.1, 116.0, 110.0, 16.7. HRMS (m/z): calcd for C10H12N3 (M+H) 174.1031. found 174.1026. Peet & Sunder (1986) Heterocycles 24:3213-3221.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe filtrate was evaporated to dryness
  3. custompurified by flash chromatography (EtOAc/Hexanes=1:1, Rf=0.5)

Sources & evidence

ORD record
ord-2fbf708ad3194c8baebbbfa98f2f77bb
Source dataset
uspto-grants-2016_05
Patent number
US09345703B2

Linked notes

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