Methanol → HCID 56942892, compound

HRID 1843890Notes

Reaction equation

HRID 1843890 reaction equation
[Br-].[Br-].[Br-].B.C[O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][N:13]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[CH3:24])[C:14]2=[O:17])=[CH:9][CH:8]=1.CO>C(Cl)Cl>[OH:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][N:13]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[CH3:24])[C:14]2=[O:17])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 56942891HCID 56942891, compoundHCID 178419136HCID 178419136, compound

Product 1

HCID 56942892HCID 56942892, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1M solution of boran tri-bromide in DCM (0.839 mL, 0.839 mmol) was added to a stirred solution of 7-methoxy-2-(4-methyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (26A: 90 mg, 0.335 mmol) in DCM (3 mL) at 0° C. The resulting mixture was stirred at room temperature for 3 hours. The reaction was monitored by TLC (5% methanol in DCM). The reaction mixture was quenched with chilled water and extracted with DCM. The organic layer was washed with NaHCO3 solution, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (3% methanol in DCM) afforded 40 mg of the product (47% yield).

Workup

  1. customThe reaction mixture was quenched with chilled water
  2. extractionextracted with DCM
  3. washThe organic layer was washed with NaHCO3 solution, brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (3% methanol in DCM)

Sources & evidence

ORD record
ord-230f29b64feb453eb5144ba774353d66
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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