N,N-Dimethylpropargylamine → HCID 67155703, compound

HRID 2196677Notes

Reaction equation

HRID 2196677 reaction equation
[F:1][C:2]1[C:29]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:33])=[O:32])=[CH:28][CH:27]=[C:26]([F:37])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14](I)[N:13]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:10]2=[N:11][CH:12]=1)=[O:5].[CH3:38][N:39]([CH3:43])[CH2:40][C:41]#[CH:42]>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:38][N:39]([CH3:43])[CH2:40][C:41]#[C:42][C:14]1[N:13]([S:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[C:10]2=[N:11][CH:12]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:26]([F:37])=[CH:27][CH:28]=[C:29]([NH:30][S:31]([CH2:34][CH2:35][CH3:36])(=[O:32])=[O:33])[C:2]=3[F:1])[CH:8]=[C:9]2[CH:15]=1

Participants

5

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 67155817HCID 67155817, compound

Product 1

HCID 67155703HCID 67155703, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

A solution of 2,6-difluoro-N-(2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (91 mg, 0.14 mmol, 1.0 eq.), N,N-dimethylprop-2-yn-1-amine (2.7 eq.), CuI (0.2 eq.) and PdCl2(PPh3)2 (0.2 eq.) in 1:1 TEA/THF (8 mL) was degassed under argon for 10 minutes. The mixture was heated to 60° C. for 16 hours, and the volatiles were removed under reduced pressure. The resulting residue was diluted with EtOAc and water and filtered through GF/F paper. The layers were separated. The organic layer was dried (MgSO4) and purified by silica gel chromatography (eluting with 100% EtOAc) to afford N-(2-(3-(dimethylamino)prop-1-ynyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide as an oil (54 mg, 64%).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. additionThe resulting residue was diluted with EtOAc and water
  3. filtrationfiltered through GF/F paper
  4. customThe layers were separated
  5. dry with materialThe organic layer was dried (MgSO4)
  6. custompurified by silica gel chromatography (eluting with 100% EtOAc)

Sources & evidence

ORD record
ord-d9db39359b804b1b928add071689f9f1
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

Loading…