Propargyl bromide → HCID 59835761, compound

HRID 1916716Notes

Reaction equation

HRID 1916716 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][C:9]#[CH:10].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]#[C:25][C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[N:31]([CH2:35][CH2:36][NH:37][CH2:38][CH:39]3[CH2:41][CH2:40]3)[CH:30]=[CH:29]4)=[N:22][CH:23]=2)=[CH:14][CH:13]=1>CN(C=O)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]#[C:25][C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[N:31]([CH2:35][CH2:36][N:37]([CH2:38][CH:39]3[CH2:40][CH2:41]3)[CH2:10][C:9]#[CH:8])[CH:30]=[CH:29]4)=[N:22][CH:23]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 59835834(2-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl)-cyclopropylmethyl-amine

Product 1

HCID 59835761HCID 59835761, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

45 mg (0.33 mmol) K2CO3 and 13 μL (0.18 mmol) 3-bromo-propyne are added at RT to a solution of 70 mg (0.16 mmol) (2-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl)-cyclopropylmethyl-amine in 2 mL DMF and the reaction mixture is stirred for 4 h at RT. The mixture is evaporated down i. vac., the residue is taken up in water, extracted exhaustively with DCM and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (Alox, cyc/EtOAc 4:1).

Workup

  1. customThe mixture is evaporated down i
  2. extractionextracted exhaustively with DCM
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customis purified by chromatography (Alox, cyc/EtOAc 4:1)

Sources & evidence

ORD record
ord-c6a03cbd963240678ee8fb810c8f1717
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

Loading…