Potassium Carbonate → 5-(5-chloro-2-thienyl)-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

HRID 2267529Notes

Reaction equation

HRID 2267529 reaction equation
N1([CH2:6][CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[C:25]4[C:20](=[C:21]([C:31]([NH2:33])=[O:32])[CH:22]=[C:23](C5C=CSC=5)[CH:24]=4)[NH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])CCCC1.[Cl:34][C:35]1[S:39][C:38](B(O)O)=[CH:37][CH:36]=1.C(=O)([O-])[O-].[K+].[K+].O1[CH2:54][CH2:53]OCC1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:34][C:35]1[S:39][C:38]([C:23]2[CH:24]=[C:25]3[C:20](=[C:21]([C:31]([NH2:33])=[O:32])[CH:22]=2)[NH:19][CH:18]=[C:17]3[CH:14]2[CH2:13][CH2:12][N:11]([S:8]([CH2:7][CH2:6][CH2:16][N:11]3[CH2:54][CH2:53][CH2:13][CH2:12]3)(=[O:10])=[O:9])[CH2:16][CH2:15]2)=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-Dioxane2×HCID 27343245-Chlorothiophene-2-boronic acidHCID 116200533-(1-{[2-(1-pyrrolidinyl)ethyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 115047545-(5-chloro-2-thienyl)-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

The title compound was prepared following the general procedure described in intermediate 16. Thus, 15-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (95 mg, 0.19 mmol) in dioxane (3 mL) and water (1 mL), 5-chloro-2-thienylboronic acid (123 mg, 0.76 mmol), Pd(PPh3)4 (22.2 mg, 10%) and potassium carbonate (211 mg, 1.52 mmol) in dioxane (3.0 mL) and water (1.0 mL) were reacted to form the desired product which was purified by reverse phase HPLC eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to give the title compound (11 mg, 11%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-8d29cd79ba3c4f86a1efb03bb449f4bd
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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