Methanol → HCID 56942892, compound

HRID 1843913Notes

Reaction equation

HRID 1843913 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 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Boran tri-bromide in DCM (10 mL) was added to a stirred solution of 7-methoxy-2-(4-methyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (35A: 1.1 g, 4.104 mmol) in DCM (20 mL) at 0° C. The resulting mixture was stirred at room temperature for 3 hours. The reaction was monitored by TLC (10% methanol in DCM). The reaction mixture was quenched with methanol and concentrated. The concentrate was partitioned between water and DCM. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (3% methanol in DCM) afforded 850 mg of the product (77% yield).

Workup

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

Sources & evidence

ORD record
ord-689264f2c8d242a68346bd06c0f7c4c1
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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