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

HRID 1054080노트

반응식

HRID 1054080 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-2aa067969fb74bc88e9aaaa3bbdb9864
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394290B2

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