1-(2,6-Difluorophenyl)-1-[6-(2,4-difluorophenyl)-5-(hydroxymethyl)pyridin-2-yl]but-3-yn-2-one → HCID 16065181, compound

HRID 1360707Notes

Reaction equation

HRID 1360707 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[C:16]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])[N:15]=1)[C:10](=[O:13])[C:11]#[CH:12]>CN(CCN(C)C)C>[F:29][C:23]1[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:22]=1[C:16]1[N:15]2[C:14]([CH:19]=[CH:18][C:17]=1[CH2:20][OH:21])=[C:9]([C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[C:10](=[O:13])[CH:11]=[CH:12]2

Participants

3

Reactant 1

HCID 577003771-(2,6-Difluorophenyl)-1-[6-(2,4-difluorophenyl)-5-(hydroxymethyl)pyridin-2-yl]but-3-yn-2-one

Product 1

HCID 16065181HCID 16065181, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8037N,N,N',N'-TetramethylethylenediamineSolvent

Procedure

To a solution of 1-(2,6-difluorophenyl)-1-[6-(2,4-difluorophenyl)-5-(hydroxymethyl)pyridin-2-yl]but-3-yn-2-one (from Step E above, 1.0 g) in TMEDA was heated to 110° C. until reaction completed. The mixture was concentrated and purified by silica gel (100% acetone) to give title compound as a yellow solid (0.46 g).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel (100% acetone)

Sources & evidence

ORD record
ord-f36db26aa3834fb09874c1937aa7f15d
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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