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Ethyl Acetate → methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(2-formyl-3-thienyl)-1H-indole-6-carboxylate

HRID 1714040
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HRID 1714040 반응식
Br[C:2]1[N:3]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.[CH:29]([C:31]1[S:32][CH:33]=[CH:34][C:35]=1B(O)O)=[O:30].C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:25]([O:24][C:22](=[O:23])[CH2:21][N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2)[C:10]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:2]1[C:35]1[CH:34]=[CH:33][S:32][C:31]=1[CH:29]=[O:30])([CH3:28])([CH3:27])[CH3:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27734262-Formyl-3-thiopheneboronic acidHCID 299433152-Bromo-1-tert-butoxycarbonylmethyl-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

생성물 1

HCID 86604968methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(2-formyl-3-thienyl)-1H-indole-6-carboxylate

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 312751,4-Dioxane용매

실험 절차

Methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate (prepared as described in Example 1, Step 1) and (2-formyl-3-thienyl) boronic acid (1.5 eq) were dissolved in dioxane (0.07 M) and 2M aqueous Na2CO3 (6 eq) was added. The solution was degassed by bubbling argon, Pd(PPh3)2Cl2 (0.2 eq) was added, and the reaction mixture was refluxed for 45 min; after cooling EtOAc was added and the solution washed with water and brine, dried over Na2SO4 and concentrated. The title compound was isolated by chromatography (PE/EtOAc 9:1). Yield (84%); MS (ES+) m/z 504 (M+Na)+.

후처리

  1. customThe solution was degassed
  2. additionwas added
  3. temperaturethe reaction mixture was refluxed for 45 min
  4. additionwas added
  5. washthe solution washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f215ef09e56f4f488a04dfb2fe4ce3c5
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795247B2

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