2-Amino-5-cyanopyridine → 2-(5-Bromofuran-2-yl)-imidazo[1,2-a]pyridine-6-carbonitrile

HRID 2113554Notes

Reaction equation

HRID 2113554 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.Br[CH2:11][C:12]([C:14]1[O:15][C:16]([Br:19])=[CH:17][CH:18]=1)=O>C(O)C>[Br:19][C:16]1[O:15][C:14]([C:12]2[N:1]=[C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]3[CH:11]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 8182602-Amino-5-cyanopyridineHCID 125376692-Bromo-1-(5-bromofuran-2-yl)ethan-1-one

Product 1

HCID 692538532-(5-Bromofuran-2-yl)-imidazo[1,2-a]pyridine-6-carbonitrileYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-Amino-nicotinonitrile (1.19 g, 10 mmol) and 2-Bromo-1-(5-bromofuran-2-yl)-ethanone (2.66 g, 10 mmol) in ethanol (50 mL) was refluxed for 24 h. The precipitate was filtered and neutralized with aqueous NaHCO3 solution. The precipitate was filtered and dried to furnish 3a in 74% yield, mp 212-214° C. (EtOH). 1H NMR (DMSO-d6); δ 6.75 (d, J=3.6 Hz, 1H), 6.98 (d, J=3.6 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 8.29 (s, 1H), 9.30 (s, 1H). 13C NMR; δ 150.5, 144.2, 137.3, 134.3, 125.4, 121.9, 117.2, 116.9, 113.9, 110.4, 109.8, 97.2. MS (m/z, rel.int.); 288 (M+, 100), 161 (8). Anal. Calcd. for 3a (C12H6BrN3O): C % 50.03, H % 2.10. Found: C % 49.97, H % 2.17.

Workup

  1. temperaturewas refluxed for 24 h
  2. filtrationThe precipitate was filtered
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-cca7e578d3e5470bacc2afa162f0338b
Source dataset
uspto-grants-2008_10
Patent number
US07432278B2

Reaction notes

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