Aluminum(III) Chloride → 2-(2,3-Difluoro-phenyl)-1-[5-(3-dimethylamino-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-ethanone

HRID 269483Notes

Reaction equation

HRID 269483 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][NH:12][C:9]2=[N:10][CH:11]=1.[Al+3].[Cl-].[Cl-].[Cl-].[F:20][C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:28][C:29](Cl)=[O:30]>C(Cl)Cl>[F:20][C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:28][C:29]([C:14]1[C:8]2[C:9](=[N:10][CH:11]=[C:6]([C:5]#[C:4][CH2:3][N:2]([CH3:1])[CH3:15])[CH:7]=2)[NH:12][CH:13]=1)=[O:30]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 25110985(2,3-Difluorophenyl)acetyl chlorideHCID 59832182Dimethyl-[3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-prop-2-ynyl]-amine

Product 1

HCID 598322022-(2,3-Difluoro-phenyl)-1-[5-(3-dimethylamino-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

189 mg of crude Dimethyl-[3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-prop-2-ynyl]-amine was stirred in 5 ml of DCM with AlCl3 (4 equivalents) for 30 minutes. Two equivalents of (2,3-Difluoro-phenyl)-acetyl chloride were added and the reaction was stirred in a sealed tube overnight. The LC/MS showed the reaction to be complete and was worked-up under standard conditions. Normal phase column chromatography yielded 101 mg of 2-(2,3-Difluoro-phenyl)-1-[5-(3-dimethylamino-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-ethanone with a yield over two steps of 33%. LC/MS retention time of 1.83 minutes. M+ 354.17, M− 352.1

Workup

  1. customthe reaction

Sources & evidence

ORD record
ord-97b5414125a94f1fa05a61292c482fa6
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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