Iodoethane → HCID 21880579, compound

HRID 899322Notes

Reaction equation

HRID 899322 reaction equation
[CH2:1](I)[CH3:2].[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:26]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[C:14]2[N:15]=[C:16]([CH3:25])[N:17]([CH2:20][C:21]([F:24])([F:23])[F:22])[C:18](=[O:19])[C:13]2=[N:12]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:26]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:1][CH3:2])=[CH:31][CH:32]=2)=[C:14]2[N:15]=[C:16]([CH3:25])[N:17]([CH2:20][C:21]([F:24])([F:22])[F:23])[C:18](=[O:19])[C:13]2=[N:12]1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 135839338HCID 135839338, compound

Product 1

HCID 21880579HCID 21880579, compound

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Ethyl iodide (88 μL, 1.1 mmol) was added to a mixture of 2-(2-chlorophenyl)-3-(4-hydroxyphenyl)-5-methyl-6-(2,2,2-trifluoroethyl)-2,6-dihydropyrazolo[4,3-d]pyrimidin-7-one (6A-1, 50 mg, 0.11 mmol), Cs2CO3 (55 mg, 0.17 mmol) in NMP (2 ml) at 85° C. The reaction mixture was stirred at this temperature for 5 h, cooled to room temperature, and diluted with 0.5 M citric acid. The aqueous solution was extracted with EtOAc (2×), and the combined organic extracts were washed with 1 M K2CO3, saturated aqueous NaCl, dried, and concentrated in vacuo. The crude residue was purified on a Chromatotron using 1 mm plates and 33% EtOAc/hexanes to give the desired product 7A-1 as an amorphous glass: MS (m/z) 435.4 (M+H)+; 1H NMR (400 MHz, CD2Cl2): δ 7.61-7.46 (m, 4H), 7.25-7.20 (m, 2H), 6.74-6.69 (m, 2H), 5.02 (q, J=7.1 Hz, 2H), 2.65 (s, 3H).

Workup

  1. extractionThe aqueous solution was extracted with EtOAc (2×)
  2. washthe combined organic extracts were washed with 1 M K2CO3, saturated aqueous NaCl
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified on a Chromatotron

Sources & evidence

ORD record
ord-2b5ac34cf8a24e768d3e0709ca169df0
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

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