Water → 2-((Pyridin-2-ylthio)methyl)-3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo-[1,2-a]pyridine

HRID 1048730ノート

反応式

HRID 1048730 の反応式
Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[C:11]=1[C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[SH:30].C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C>[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30][CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[C:11]=1[C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 90031792HCID 90031792、化合物HCID 178418616HCID 178418616、化合物

生成物 1

HCID 900320492-((Pyridin-2-ylthio)methyl)-3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo-[1,2-a]pyridine収率 74.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

150 mg (0.421 mmol) of 2-(chloromethyl)-3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridine were dissolved in 5 ml of acetonitrile followed by the addition of 96 mg (0.842 mmol) of pyridine-2-thiol and 274 mg (0.842 mmol) of cesium carbonate. The solvent was stirred at r.t. for 2 h 30 min. The mixture was then poured into 40 ml of water, and then extracted 3 times with 15 ml of ethyl acetate. The collected organic phases were washed with 30 ml of a saturated sodium hydrogencarbonate solution, with 30 ml of brine and then were dried on Na2SO4 which was then removed by filtration and the obtained filtrate was concentrated in vacuo. The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: heptane/ethyl acetate gradient, 80% to 70% of heptane, v/v). 129 mg (yield=74%) of 2-((pyridin-2-ylthio)methyl)-3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo-[1,2-a]pyridine were obtained as a beige solid. LC-MS: m/z=410 (MH+) UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 8.70 (d, J=6.7 Hz, 1H), 8.52-8.37 (m, 1H), 8.02 (s, 1H), 7.91 (d, J=7.6 Hz, 1H), 7.71 (dd, J=41.7, 4.5 Hz, 4H), 7.43 (s, 2H), 7.13 (d, J=1.1 Hz, 2H), 4.73 (s, 2H).

後処理

  1. extractionextracted 3 times with 15 ml of ethyl acetate
  2. washThe collected organic phases were washed with 30 ml of a saturated sodium hydrogencarbonate solution, with 30 ml of brine
  3. customwere dried on Na2SO4 which
  4. customwas then removed by filtration
  5. concentrationthe obtained filtrate was concentrated in vacuo
  6. customThe crude residue was purified by flash chromatography on a silica gel cartridge (eluent: heptane/ethyl acetate gradient, 80% to 70% of heptane, v/v)

出典と根拠

ORDレコード
ord-329d0b4582f44aeea26e203f302013df
出典データセット
uspto-grants-2016_07
特許番号
US09381191B2

反応ノート

読み込み中…