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

HRID 646166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646166
[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]

Komponenten

8

Edukt 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

Produkt 1

HCID 686979183-Chloro-5-(5-chloropyrid-2-yl)-1-(4-cyclopentoxyphenyl)-1H-indole-2-carboxylic acid ethyl esterAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-77ea74934f4742ff9ddb1a6903028580
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705023B2

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