Cesium carbonate → 1-(3-Amino-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridin-2-yl)-2,2-dimethylpropan-1-one

HRID 8806

Reaction equation

HRID 8806 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:13][C:12](=[O:14])[C:11]([C:15]#[N:16])=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34]>CN(C=O)C.C(OCC)(=O)C>[NH2:16][C:15]1[C:11]2[C:12](=[N:13][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[C:9]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[CH:10]=2)[O:14][C:31]=1[C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 21642BromopinacoloneHCID 219849076-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 104783311-(3-Amino-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridin-2-yl)-2,2-dimethylpropan-1-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.5 g (1.46 mmol) of the product of Step B in 10 mL DMF was added 0.954 g Cs2CO3 and 0.197 mL of 1-bromopinacolone. The reaction was stirred 17 hours at room temperature at which point the reaction mixture was diluted with ethyl acetate and washed with saturated NaCl/NaHCO3 solution (1:1). The residue from the concentrated solution was purified via silica gel flash chromatography eluting with a gradient of 0 to 75% ethyl acetate/hexane to afford the title compound. HPLC-MS: 439.1 (M+1), 441.1 (M+3); Rt=4.53 min.

Workup

  1. washwashed with saturated NaCl/NaHCO3 solution (1:1)
  2. customThe residue from the concentrated solution was purified via silica gel flash chromatography
  3. washeluting with a gradient of 0 to 75% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1947bd8bee374badb21ae13f23022d0b
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Linked notes

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