Cesium carbonate → Ethyl 5-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]-1-(tetrahydro-2-furanylmethyl)-1H-indole-2-carboxylate

HRID 1006249

반응식

HRID 1006249 반응식
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19]2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:37][CH:38]1[CH2:42][CH2:41][CH2:40][O:39]1>CN(C)C=O>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH2:37][CH:38]1[CH2:42][CH2:41][CH2:40][O:39]1)[C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19]2

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 22676745ethyl 5-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]-1H-indole-2-carboxylate

생성물 1

HCID 22676841Ethyl 5-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]-1-(tetrahydro-2-furanylmethyl)-1H-indole-2-carboxylate수율 40.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of ethyl 5-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]-1H-indole-2-carboxylate 220 (40.7 mg, 0.100 mmol) in N,N-dimethylformamide (0.9 mL) was added to a stirred mixture of cesium carbonate (325 mg, 1.00 mmol) and 2-(bromomethyl)tetrahydrofuran (19.8 mg, 0.120 mmol) in N,N-dimethylformamide (2.4 mL). The reaction was stirred for 16 h and then the mixture was filtered though a plug (500 mg) of silica gel using ethyl acetate to rinse. The filtrate was concentrated in vacuo and then reverse phase preparative HPLC chromatography gave 19.8 mg of product (retention time=2.4 min.). This material was taken to the next reaction without further purification or analysis.

후처리

  1. filtrationthe mixture was filtered though a plug (500 mg) of silica gel
  2. washto rinse
  3. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-731844116c9541c0b2d22f19a11c0e2e
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787651B2

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