Tert-Butyl isocyanide → HCID 90389135, compound

HRID 2203406Notes

Reaction equation

HRID 2203406 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]=[CH2:9])=[N:6][CH:7]=1.[C:10]([N+:14]#[C-:15])([CH3:13])([CH3:12])[CH3:11]>CO.FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:15]([NH:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:9][N:8]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 23577Tert-Butyl isocyanideHCID 89545313HCID 89545313, compound

Product 1

HCID 90389135HCID 90389135, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 5-bromo-N-methylenepyridin-2-amine (0.85 g, 4.6 mmol) in methanol (20 mL) was added tert-butyl isocyanide (1.14 mL, 10.1 mmol) and trifluoroacetic acid (˜3 drops). The reaction mixture was heated at reflux for 2 h, after which point a clear solution was obtained. The mixture was allowed to cool to ambient temperature and was concentrated in vacuo. The residue was purified by column chromatography eluting with a 0-100% gradient ethyl acetate in hexanes to afford 6-bromo-N-(tert-butyl)imidazo[1,2-a]pyridin-3-amine as a beige solid in 78% yield (0.956 g): 1H NMR (300 MHz, CDCl3) δ8.31 (br s, 1H), 7.41-7.33 (m, 1H), 7.29 (s, 1H), 7.17-7.10 (m, 1H), 2.70 (br s, 1H), 1.16 (s, 9H); MS (ES+) m/z 267.9 (M+1), 270.0 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. customwas obtained
  4. concentrationwas concentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with a 0-100% gradient ethyl acetate in hexanes

Sources & evidence

ORD record
ord-925943c77c3c430ca25e61a01e7adb6b
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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