Ethyl Acetate → HCID 56942730, compound

HRID 1843846Notes

Reaction equation

HRID 1843846 reaction equation
[Br-].[Br-].[Br-].B.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24])[CH2:11][CH2:10]2.C(OC(=O)C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCCCCC.CO>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24])[CH2:11][CH2:10]2

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 56942729HCID 56942729, compoundHCID 178419136HCID 178419136, compound2×

Product 1

HCID 56942730HCID 56942730, compoundYield 9.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

Boran tri-bromide (0.68 mL, 0.6715 mmol) was added dropwise to a solution of 6-methoxy-2-(4-methyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (11A: 0.120 g, 0.4477 mmol) in DCM (2 mL) at −78° C. over a period of 5 minutes under nitrogen atmosphere. The resulting mixture was stirred at room temperature for 16 hours. The reaction was monitored by TLC (80% ethylacetate in hexane). Since unreacted starting material was observed, a further 1.5 equivalents of boran tri-bromide (0.68 mL, 0.6715 mmol) was added and stirring was continued for a further 3 hours at room temperature. Methanol and saturated NaHCO3 were added to the reaction mixture and diluted with DCM. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (80% ethylacetate in hexane), followed by preparative TLC afforded 0.011 g of the product (9.7% yield).

Workup

  1. stirringstirring
  2. waitwas continued for a further 3 hours at room temperature
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (80% ethylacetate in hexane)

Sources & evidence

ORD record
ord-4e9cce39a2334159abd2b96e96effd2a
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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