3-formyl-N-methyl-1H-indole-2-carboxamide → N-methyl-3-vinyl-1H-indole-2-carboxamide

HRID 2097180노트

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HRID 2097180 반응식
[CH2:1]([Li])CCC.[CH:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[C:17]([NH:19][CH3:20])=[O:18])=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:20][NH:19][C:17]([C:9]1[NH:10][C:11]2[C:16]([C:8]=1[CH:6]=[CH2:1])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:18]

참가 물질

5

반응물 2

HCID 592775763-formyl-N-methyl-1H-indole-2-carboxamideHCID 178418339Butyllithium

생성물 1

HCID 59277607N-methyl-3-vinyl-1H-indole-2-carboxamide

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

n-Butyllithium (2.5M in hexanes) (48.6 mL, 121.7 mmol) was added dropwise to an ice-cooled solution of methyl triphenylphosphoniumbromide (43.5 g, 121.7 mmol) in THF (500 mL). The mixture was stirred at 0° C. for 1 h then at rt for 2 h. 3-Formyl-N-methyl-1H-indole-2-carboxamide (1.96 g, 9.7 mmol) in THF (100 mL) was added and the mixture stirred at rt for 2 h. The solvent was evaporated and the residue dissolved in ethyl acetate and washed twice with water. The organic phase was dried over magnesium bromide and evaporated in vacuo. The crude mixture was chromatographed over silica gel eluting with 40% ethyl acetate in hexanes to afford the title compound (730 mg (38%). 1H NMR (300 MHz, DMSO-d6) δ 11.48 (s, 1H), 8.04 (s, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.33 (d, J=18 Hz, 1H), 7.22 (t, J=7.6 Hz, 1H), 7.09 (t, J=7.2 Hz, 1H), 5.77 (d, J=18.4 Hz, 1H), 5.27 (d, J=11.6 Hz, 1H), 2.81 (s, 3H).

후처리

  1. waitat rt for 2 h
  2. stirringthe mixture stirred at rt for 2 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed twice with water
  6. dry with materialThe organic phase was dried over magnesium bromide
  7. customevaporated in vacuo
  8. customThe crude mixture was chromatographed over silica gel eluting with 40% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-5c9b60afe413441b9e144ca98632eade
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450307B2

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