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

HRID 646166Notes

Reaction equation

HRID 646166 reaction equation
[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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-77ea74934f4742ff9ddb1a6903028580
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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