Water → HCID 89443820, compound

HRID 1771717Notes

Reaction equation

HRID 1771717 reaction equation
[F:1][C:2]1[C:24]([OH:25])=[CH:23][CH:22]=[C:21]([F:26])[C:3]=1[NH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH:13]=1)[C:9]#[N:10].C([O-])([O-])=O.[K+].[K+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].O>CN(C=O)C>[C:9]([C:8]1[CH:7]=[C:6]([CH2:5][NH:4][C:3]2[C:2]([F:1])=[C:24]([CH:23]=[CH:22][C:21]=2[F:26])[O:25][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH:11]=1)#[N:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 89443808HCID 89443808, compound

Product 1

HCID 89443820HCID 89443820, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[(2,6-Difluoro-3-hydroxy-anilino)methyl]-5-(3-fluorophenyl)benzonitrile (280 mg, 0.8 mmol, 1 eq) in DMF (10 mL) was added K2CO3 (550 mg, 4 mmol, 5 eq). The solution was stirred at room temperature for 30 min, then ethyl bromoacetate (200 mg, 1.2 mmol, 1.5 eq) was added dropwise. The reaction was stirred overnight, then water was added and the aqueous phase extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 15:1) to give the title compound as colorless oil (300 mg, 86%).

Workup

  1. stirringThe reaction was stirred overnight
  2. extractionthe aqueous phase extracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue obtained
  7. customwas purified by column chromatography (petroleum ether:EtOAc, 15:1)

Sources & evidence

ORD record
ord-2ca288e9fc594f7484f36a2662dd8e9d
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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