HCID 89524829, compound → HCID 53403113, compound

HRID 920228Notes

Reaction equation

HRID 920228 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[N:13][CH:12]=[CH:11]2)=[O:5].[CH3:17][Mg]Br>C1COCC1>[CH:14]1[C:15]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[C:4](=[O:5])[CH3:17])[CH:11]=[CH:12][N:13]=1

Participants

4

Reactant 2

HCID 89524829HCID 89524829, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 53403113HCID 53403113, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of N-methoxy-N-methylisoquinoline-8-carboxamide (1.04 g, 4.81 mmol) in THF (40.1 ml) at 0° C. was treated with methylmagnesium bromide (11.22 ml, 33.7 mmol) in THF. Reaction was stirred at 0° C. for 1 hours before quenching with a saturated ammonium chloride solution (5 mL). After reaching RT, solution extracted with EtOAc (3×75 mL). Combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. Purified by normal phase chromatography (0-50% EtOAc in hexane) to yield 1-(isoquinolin-8-yl)ethanone as an oil.

Workup

  1. customReaction
  2. custombefore quenching with a saturated ammonium chloride solution (5 mL)
  3. customAfter reaching RT
  4. extractionsolution extracted with EtOAc (3×75 mL)
  5. washCombined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurified by normal phase chromatography (0-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-05039fb0502245719a9dd077b8676fc2
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

Loading…