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Dimethyl Sulfoxide → Methyl 1-allyl-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate

HRID 1518257
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인쇄 미리보기

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HRID 1518257 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][OH:40])[CH:12]=[CH2:13].CCN(CC)CC>C(Cl)Cl>[CH2:11]([N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH:39]=[O:40])[CH:12]=[CH2:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68702775Methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate

생성물 1

HCID 86637858Methyl 1-allyl-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
3회

실험 절차

Oxalyl chloride (2.5 eq., 2M solution in DCM) was added at −70° C. under nitrogen atmosphere to a solution of DMSO (5 eq.) in anhydrous DCM and the mixture was stirred for 30 min; a solution of methyl 1-allyl-3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate in DCM was then added and stirring was continued at the same temperature for 30 min. before NEt3 (8 eq.) was added. After stirring for 20 min. at 0° C. the mixture was diluted with DCM, then washed with water, 1N HCl, saturated aq. NaHCO3 solution and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The residual material was used in the next step without purification. MS (ES+): 402.2 (M+H+).

후처리

  1. stirringstirring
  2. additionwas added
  3. stirringAfter stirring for 20 min. at 0° C. the mixture
  4. washwashed with water, 1N HCl, saturated aq. NaHCO3 solution and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated in vacuo
  7. customThe residual material was used in the next step without purification

출처 및 근거

ORD 기록
ord-1763e5c80cc94d4d83d1e3aa9dc0335c
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08232390B2

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