Cesium carbonate → HCID 89444009, compound

HRID 1771809Notes

Reaction equation

HRID 1771809 reaction equation
[F:1][C:2]1[C:3]([NH:11][CH2:12][C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[CH:16]=[CH:15][C:14]=2[F:26])=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[C:5]#[N:6].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:34][C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36]>CC(C)=O>[C:5]([C:4]1[C:3]([NH:11][CH2:12][C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[CH:16]=[CH:15][C:14]=2[F:26])=[C:2]([F:1])[CH:9]=[CH:8][C:7]=1[O:10][CH2:34][C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])#[N:6]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 121593Isopropyl bromoacetateHCID 89445280HCID 89445280, compound

Product 1

HCID 89444009HCID 89444009, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-fluoro-2-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-6-hydroxy-benzonitrile (360 mg, 1.0 mmol, 1 eq) in acetone was added Cs2CO3 (651.6 mg, 2.0 mmol, 2 eq). The reaction was stirred for 30 min at room temperature then isopropyl 2-bromoacetate (221 mg, 1.2 mmol, 1.2 eq) was added. The reaction was stirred for a further 2 h, then quenched with water and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 50:1 to 10:1) to give the title compound as a colorless oil (270 mg, 59%).

Workup

  1. stirringThe reaction was stirred for a further 2 h
  2. customquenched with water
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by column chromatography (petroleum ether:EtOAc, 50:1 to 10:1)

Sources & evidence

ORD record
ord-83b7d6c309f04561a823698465455647
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…