Methyl iodide → Methyl 4-(5-benzyloxycarbonyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate

HRID 1975417노트

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HRID 1975417 반응식
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:36]>CN(C)C=O.O.Cl>[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:36])[CH:15]=[C:14]2[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10252039HCID 10252039, 화합물

생성물 1

HCID 10343359Methyl 4-(5-benzyloxycarbonyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate수율 89.1%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
5 °C

실험 절차

A solution of methyl 4-(5-benzyloxycarbonylindol-3-ylmethyl)-3-methoxybenzoate (46.1 g) in N,N-dimethylformamide (200 mL) was added to a slurry of sodium hydride (2.83 g) in N,N-dimethylformamide (300 mL) at 5° C. under a nitrogen atmosphere. The mixture was stirred for 30 minutes at 5° C., then was treated with iodomethane (16.6 g), allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was then poured into ice/water (400 mL), diluted with water (250 mL) and 1N hydrochloric acid (250 mL). The resulting aqueous solution was extracted with ethyl acetate. The combined organic extract was washed (1N hydrochloric acid, water, brine), dried (MgSO4), filtered and evaporated. The residue was triturated with warm diethyl ether and filtered to give methyl 4-(5-benzyloxycarbonyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate as an ivory solid (42.4 g, 89%); partial NMR (300 MHz, CDCl3): 3.75 (s, 3H, NCH3), 3.87 (s, 3H, CO2CH3), 3.90 (s, 3H, OCH3), 4.12 (s, 2H, CH2), 5.36 (s, 2H, OCH2), 6.82 (s, 1H, indole-H(2)), 8.38 (d, 1H, indole-H(4)).

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 16 hours
  3. extractionThe resulting aqueous solution was extracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed (1N hydrochloric acid, water, brine)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was triturated with warm diethyl ether
  10. filtrationfiltered

출처 및 근거

ORD 기록
ord-1ba73776333e4a82ab5523697a467bd3
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05286740

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