Potassium Phosphate, Tribasic → 3-Chloro-5-(5-chloropyrid-2-yl)-1-(4-cyclopentoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 646166노트

반응식

HRID 646166 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:21][CH:20]=2)[C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[Cl:31][C:32]1[CH:33]=[CH:34][C:35](OS(C(F)(F)F)(=O)=O)=[N:36][CH:37]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1COCC1.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:21][CH:20]=2)[C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][C:11]([C:35]1[CH:34]=[CH:33][C:32]([Cl:31])=[CH:37][N:36]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 117802885-Chloropyridin-2-yl trifluoromethanesulfonateHCID 686986803-Chloro-5-(dihydroxyboryl)-1-(4-cyclopentoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester

생성물 1

HCID 686979183-Chloro-5-(5-chloropyrid-2-yl)-1-(4-cyclopentoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester수율 40.4%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred suspension of 3-chloro-5-(dihydroxyboryl)-1-(4-cyclopentoxyphenyl)-1H-indole-2-carboxylic acid ethyl ester (see step (b) above; 214 mg, 0.5 mmol), trifluoromethanesulfonic acid 5-chloropyrid-2-yl ester (see step (c) above; 130.0 mg, 0.5 mmol) and K3PO4 (200 mg, 0.95 mmol) in THF (2.0 mL) under argon at room temperature was added a mixture of Pd(OAc)2 (23.0 mg, 0.1 mmol) and tricyclohexylphosphine (34 mg, 0.12 mmol) in THF (2.0 mL). The reaction was stirred at ambient temperature for 12 h, diluted with Et2O (10 mL), washed with brine and dried (Na2SO4). Concentration and purification by chromatography afforded the sub-title product (100 mg, 40%).

후처리

  1. additionwas added
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration and purification by chromatography

출처 및 근거

ORD 기록
ord-77ea74934f4742ff9ddb1a6903028580
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705023B2

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