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Methyl iodide → (+/-)-tert-Butyl-4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-methoxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174080
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HRID 2174080 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([C:14]3[C:22]([O:23][CH3:24])=[CH:21][C:20]([CH3:25])=[C:19]4[C:15]=3[CH:16]=[CH:17][N:18]4[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([OH:13])[CH3:12])=[N:8][C:7]=2[CH:33]=1)#[N:2].[CH3:34]I.[H-].[Na+]>CN(C=O)C>[C:29]([O:28][C:26]([N:18]1[C:19]2[C:15](=[C:14]([C:11]([C:9]3[O:10][C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:33][C:7]=4[N:8]=3)([O:13][CH3:34])[CH3:12])[C:22]([O:23][CH3:24])=[CH:21][C:20]=2[CH3:25])[CH:16]=[CH:17]1)=[O:27])([CH3:32])([CH3:31])[CH3:30]
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5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86701712tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-hydroxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

생성물 1

HCID 86701714(+/-)-tert-Butyl-4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-methoxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide
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온도
0 °C

실험 절차

To a solution of tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-hydroxyethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (250 mg, 0.559 mmol) in DMF (5.7 mL) at 0° C. was added successively MeI (0.105 mL, 1.676 mmol) and NaH (60% in mineral, 33.5 mg, 0.838 mmol). The reaction mixture was stirred at 0° C. for 1.5 h. The reaction mixture was quenched with 4 mL of saturated aq. solution of ammonium chloride and diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-30% EtOAc:heptanes) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.43 (dd, J=1.52, 0.63 Hz, 1H) 7.79-7.97 (m, 2H) 7.63 (d, J=3.79 Hz, 1H) 7.05 (d, J=3.79 Hz, 1H) 6.83 (s, 1H) 3.23 (s, 3H) 3.17 (s, 3H) 1.81-2.08 (m, 3H) 1.60 (s, 9H).

후처리

  1. customThe reaction mixture was quenched with 4 mL of saturated aq. solution of ammonium chloride
  2. additiondiluted with water and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (0-30% EtOAc:heptanes)

출처 및 근거

ORD 기록
ord-ea928dca8d3345f599f048648cfb3bb8
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09056874B2

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