Cesium fluoride → HCID 71244877, compound

HRID 2171604Notes

Reaction equation

HRID 2171604 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20][CH3:21])[C@@H:13]3[CH2:18][C:17](=[O:19])[CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:22][C:23]([Si](C)(C)C)([F:25])[F:24].[F-].[Cs+]>C1COCC1>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20][CH3:21])[C@@H:13]3[CH2:18][C:17]([OH:19])([C:23]([F:25])([F:24])[F:22])[CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 71239443HCID 71239443, compound

Product 1

HCID 71244877HCID 71244877, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-4-((3S,3aS)-3-methoxy-5-oxo-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile prepared according to example 9 (10 mg, 0.033 mmole) in THF (3 mL) at 0° C. was added trifluoromethyl-trimethyl silane (0.02 mL, 0.0396 mmol) followed by the addition of CsF (0.5 mg, 0.0033 mmol) and the reaction mixture was stirred at room temperature for 3 h. Once the starting material had disappeared (monitored by TLC), the reaction mixture was quenched with 4N HCl and extracted with diethyl ether. Organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by preparative TLC method (2% MeOH in DCM) provided the title compound.

Workup

  1. customthe reaction mixture was quenched with 4N HCl
  2. extractionextracted with diethyl ether
  3. washOrganic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by preparative TLC method (2% MeOH in DCM)

Sources & evidence

ORD record
ord-5c1d4f92bf2641bf86b70a3aa43c9779
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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