Methyl iodide → methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1-methyl-1H-indole-6-carboxylate

HRID 1807630노트

반응식

HRID 1807630 반응식
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[NH:18][C:19]2[C:24]([C:25]=1[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[CH:23][CH:22]=[C:21]([C:32]([O:34][CH3:35])=[O:33])[CH:20]=2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH3:37]>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[N:18]([CH3:37])[C:19]2[C:24]([C:25]=1[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[CH:23][CH:22]=[C:21]([C:32]([O:34][CH3:35])=[O:33])[CH:20]=2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67225298methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1H-indole-6-carboxylate

생성물 1

HCID 58317811methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1-methyl-1H-indole-6-carboxylate수율 80.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

NaH (810 mg, 32.1 mmol) was added to a solution of intermediate 2 (9.4 g, 21.4 mmol) in dry DMF. Then, iodomethane (3.64 g, 25.7 mmol) was added at room temperature. After 12 h, the reaction mixture was partitioned between water (pH 6) and AcOEt. Organic layer was dried over anhydrous Na2SO4, filtered and then evaporated. The residue was purified by silica column chromatography (gradient heptane/AcOEt 1:0 to 80:20) to yield 7.8 g (80%) of methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1-methyl-1H-indole-6-carboxylate 3: m/z=454 (M+H)+.

후처리

  1. customthe reaction mixture was partitioned between water (pH 6) and AcOEt
  2. dry with materialOrganic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica column chromatography (gradient heptane/AcOEt 1:0 to 80:20)

출처 및 근거

ORD 기록
ord-bbda16bac2334743a156ca682f43213c
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357687B2

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