Ethyl Acetate → HCID 66597239, 화합물

HRID 1627930노트

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HRID 1627930 반응식
I[C:2]1[C:7]([CH:8]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:9]([O:11][CH3:12])=[O:10])=[C:6]([CH3:18])[N:5]=[C:4]2[S:19][C:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[C:3]=12.C(=O)([O-])[O-].[K+].[K+].[Cl:32][C:33]1[C:42](B2OC(C)(C)C(C)(C)O2)=[CH:41][CH:40]=[C:39]2[C:34]=1[CH2:35][CH2:36][CH2:37][O:38]2.C(OCC)(=O)C>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:18][C:6]1[N:5]=[C:4]2[S:19][C:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[C:3]2=[C:2]([C:42]2[C:33]([Cl:32])=[C:34]3[C:39](=[CH:40][CH:41]=2)[O:38][CH2:37][CH2:36][CH2:35]3)[C:7]=1[CH:8]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:9]([O:11][CH3:12])=[O:10]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 596067632-(5-Chlorochroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66603844HCID 66603844, 화합물

생성물 1

HCID 66597239HCID 66597239, 화합물수율 34%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 18180031Water 1,2-dimethoxyethane용매

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온도
140 °C

실험 절차

To a solution of methyl 2-[4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-tert-butoxyacetate (0.075 g; 0.158 mmol) in a mixture of DME-water (3:1) (0.480 mL) were added potassium carbonate (0.066 g; 0.475 mmol), tetrakis(triphenylphosphine) palladium(0) (0.018 g; 0.016 mmol) and 2-(5-chlorochroman-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.070 g; 0.238 mmol). The solution was stirred for 30 min at 140° C. under microwave irradiation. Ethyl acetate was added to the reaction mixture and the solution was washed with brine. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (0-40%) in heptane furnished 0.027 g (34%) of the title compound as a light yellow oil.

후처리

  1. washthe solution was washed with brine
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (0-40%) in heptane

출처 및 근거

ORD 기록
ord-a586895f60494a559b68a41b9b44e419
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785638B2

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