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

HRID 2267531Notes

Reaction equation

HRID 2267531 reaction equation
N1(CCS(N2CCC(C3C4C(=C(C(N)=O)C=C(C5C=CSC=5)C=4)NC=3)CC2)(=O)=O)CCCC1.Br[C:35]1[CH:36]=[C:37]2[C:41](=[C:42]([C:44]([NH2:46])=[O:45])[CH:43]=1)[NH:40][CH:39]=[C:38]2[CH:47]1[CH2:52][CH2:51][N:50]([S:53]([CH2:56][CH2:57][CH2:58][N:59]2[CH2:63][CH2:62][CH2:61][CH2:60]2)(=[O:55])=[O:54])[CH2:49][CH2:48]1.[OH:64][CH2:65][C:66]1[S:70][C:69](B(O)O)=[CH:68][CH:67]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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>[OH:64][CH2:65][C:66]1[S:70][C:69]([C:35]2[CH:36]=[C:37]3[C:41](=[C:42]([C:44]([NH2:46])=[O:45])[CH:43]=2)[NH:40][CH:39]=[C:38]3[CH:47]2[CH2:52][CH2:51][N:50]([S:53]([CH2:56][CH2:57][CH2:58][N:59]3[CH2:63][CH2:62][CH2:61][CH2:60]3)(=[O:54])=[O:55])[CH2:49][CH2:48]2)=[CH:68][CH:67]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 43742655-HYDROXYMETHYLTHIOPHENE-2-BORONIC ACIDHCID 116200533-(1-{[2-(1-pyrrolidinyl)ethyl]sulfonyl}-4-piperidinyl)-5-(3-thienyl)-1H-indole-7-carboxamideHCID 590033005-bromo-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Product 1

HCID 116207245-[5-(hydroxymethyl)-2-thienyl]-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared following the general procedure described in intermediate 16. Thus, 5-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-(hydroxymethyl)-2-thienyl]boronic acid (120 mg, 0.76 mmol), Pd(PPh3)4 (22.2 mg, 10%) and potassium carbonate (211 mg, 1.52 mmol) were reacted to form the desired product which was purified by flash column chromatography (ethyl acetate/hexane, 1/1) to yield the desired product (25 mg, 25%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-d640780688ef4d46a97e0586f55d1647
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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