Pyrrolidine → 5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-1-(2-pyrrolidin-1-yl-ethyl)-1h-indole

HRID 1916712Notes

Reaction equation

HRID 1916712 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.CS(O[CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)=[CH:26][N:25]=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)(=O)=O>CN(C=O)C>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([C:27]2[CH:28]=[CH:29][C:24]([C:23]#[C:22][C:18]3[CH:17]=[C:16]4[C:21](=[CH:20][CH:19]=3)[N:13]([CH2:12][CH2:11][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:14]=[CH:15]4)=[N:25][CH:26]=2)=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 865946842-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl methanesulphonate

Product 1

HCID 129886555-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-1-(2-pyrrolidin-1-yl-ethyl)-1h-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.1 mL (13.3 mmol) pyrrolidine are added to a solution of 600 mg (1.33 mmol) 2-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl methanesulphonate in 12 mL DMF and the reaction mixture is stirred for 24 h at RT. The mixture is evaporated down i. vac., the residue is taken up in a little DCM and the product is purified by chromatography (silica gel, cyc/EtOAc 2:1)

Workup

  1. customThe mixture is evaporated down i
  2. customthe product is purified by chromatography (silica gel, cyc/EtOAc 2:1)

Sources & evidence

ORD record
ord-084f1d76ead449ac925d4122bff5d7f3
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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