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

HRID 646166ノート

反応式

HRID 646166 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-77ea74934f4742ff9ddb1a6903028580
出典データセット
uspto-grants-2010_04
特許番号
US07705023B2

反応ノート

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