Potassium Carbonate → Isohexane ethyl acetate

HRID 906445Notes

Reaction equation

HRID 906445 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[C:5]2[S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)(=[O:15])=[O:14].Br[CH2:30][CH:31]1[CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[C:22]([O:24][CH2:25][CH3:28])(=[O:23])[CH3:30].[CH3:11][CH2:2][CH2:3][CH:4]([CH3:9])[CH3:5].[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:30][CH:31]1[CH2:33][CH2:32]1)[CH:6]=[C:5]2[S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)(=[O:14])=[O:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 67389978HCID 67389978, compound

Product 2

HCID 21882781Isohexane ethyl acetateYield 50%HCID 67130358HCID 67130358, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of tert-butyl 4-[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfonyl]piperazine-1-carboxylate (Example 47a, 1.70 g) in 1-methyl-2-pyrrolidinone (10 mL) was treated with (bromomethyl)cyclopropane (0.41 mL) and potassium carbonate (0.796 g). The resulting mixture was stirred at 70° C. overnight. The cooled reaction mixture was partitioned between water (250 mL) and ethyl acetate. The organic was separated and the aqueous extracted with further ethyl acetate. The combined organics were washed with water (2×200 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated to dryness. The residue was purified (SiO2 chromatography, elution 10% ethyl acetate/isohexane then 50% ethyl acetate/isohexane) to afford the subtitle compound (0.890 g) as a pale yellow solid.

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between water (250 mL) and ethyl acetate
  3. customThe organic was separated
  4. extractionthe aqueous extracted with further ethyl acetate
  5. washThe combined organics were washed with water (2×200 mL) and brine (100 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified (
  10. washSiO2 chromatography, elution 10% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-92d570a7c944407a80988f3fde3ad3dc
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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