1,1'-Carbonyldiimidazole → 2-Methyl-1-(6-phenylpyridin-3-yl)propyl 1H-imidazole-1-carboxylate

HRID 1054080ノート

反応式

HRID 1054080 の反応式
[CH3:1][CH:2]([CH3:17])[CH:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)[OH:4].[CH:18]1[N:22]=[CH:21][N:20]([C:23](N2C=NC=C2)=[O:24])[CH:19]=1>C(#N)C>[N:20]1([C:23]([O:4][CH:3]([C:5]2[CH:6]=[N:7][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][CH:10]=2)[CH:2]([CH3:17])[CH3:1])=[O:24])[CH:19]=[CH:18][N:22]=[CH:21]1

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 675104242-Methyl-1-(6-phenylpyridin-3-yl)propan-1-ol

生成物 1

HCID 573298692-Methyl-1-(6-phenylpyridin-3-yl)propyl 1H-imidazole-1-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Synthesized using compound 43a (81 mg, 0.36 mmol), CDI (289 mg, 1.78 mmol) and acetonitrile (5 mL) according to Method E. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (4:1) as eluent. White solid. Yield: 90.0 mg, 90%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.95 (d, J=6.9 Hz, 3H), 1.14 (d, J=6.6 Hz, 3H), 2.37 (m, 1H), 5.70 (d, J=8.2 Hz, 1H), 7.09 (dd, J=1.6, 0.6 Hz, 1H), 7.40-7.51 (m, 4H), 7.72-7.79 (m, 2H), 7.98-8.03 (m, 2H), 8.19 (t, J=0.9 Hz, 1H), 8.71 (dd, J=2.2, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=18.7, 18.8, 33.6, 83.7, 117.2, 120.4, 127.1, 129.0, 129.5, 131.1, 131.8, 135.6, 137.2, 138.8, 148.7, 158.0; MS (ESI): m/z=322.32 [M+H]+.

後処理

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (4:1) as eluent

出典と根拠

ORDレコード
ord-2aa067969fb74bc88e9aaaa3bbdb9864
出典データセット
uspto-grants-2016_07
特許番号
US09394290B2

反応ノート

読み込み中…