Bromine → HCID 89871715, compound

HRID 572530Notes

Reaction equation

HRID 572530 reaction equation
[C:1]([O:5][CH:6]([C:11]1[N:12]([CH3:30])[C:13](=[O:29])[C:14]2[C:19]([C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[CH3:28])=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[Br:31]Br>CN(C)C=O.ClCCl>[Br:31][C:16]1[CH:15]=[C:14]2[C:19]([C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=3[CH3:28])=[C:11]([CH:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:7]([OH:9])=[O:8])[N:12]([CH3:30])[C:13]2=[O:29])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 68352842HCID 68352842, compound

Product 1

HCID 89871715HCID 89871715, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

An ice cold mixture of methyl 2-(tert-butoxy)-2-(4-(2,4-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)acetate (383 mg, 0.940 mmol) in N,N-dimethylformamide (DMF) (5.0 mL) was treated slowly with a solution of bromine (0.053 mL, 1.034 mmol) in dichloromethane (dichloromethane) (280 μl) to give an orange solution. The ice bath was removed and the mixture, which was excluded from light by wrapping the reaction vessel with aluminum foil, was stirred at ambient temperature overnight. The mixture was cooled to 0° C., quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with water, then brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (0-50% ethyl acetate/hexanes gradient) to give the impure desired product as a white solid. The solid was re-purified by reverse phase chromatography to afford the desired product as a white solid (128 mg, 28%). LC/MS (m/z) ES+=486 (M+1).

Workup

  1. customto give an orange solution
  2. customThe ice bath was removed
  3. temperatureThe mixture was cooled to 0° C.
  4. customquenched with saturated sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. washThe extracts were washed with water
  7. dry with materialbrine, dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified on silica gel (0-50% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-4d5478a6cc4c46a7acc162ea5111bc8b
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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