Methanol → HCID 66801965, compound

HRID 1844068Notes

Reaction equation

HRID 1844068 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][N:12]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:22]=3[CH3:23])[C:13]2=[O:16])=[CH:8][C:7]=1[O:24]C.CO>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][N:12]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:22]=3[CH3:23])[C:13]2=[O:16])=[CH:8][C:7]=1[OH:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 56940827HCID 56940827, compound

Product 1

HCID 66801965HCID 66801965, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

BBr3 (4.4 mL) was added to a stirred solution of 7-chloro-6-methoxy-2-(4-methylpyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (86A: 450 mg, 1.480 mmol) in DCM (10 mL) at 0° C. The resulting mixture was stirred for 14 hours at room temperature. The reaction was monitored by TLC (5% methanol in CHCl3). The mixture was slowly quenched with ice water extracted with chloroform (2×50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3), afforded 300 mg of the product (70.4% yield).

Workup

  1. customThe mixture was slowly quenched with ice water
  2. extractionextracted with chloroform (2×50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

Sources & evidence

ORD record
ord-a2f952667b9b4b208b5af3d3c5e872ac
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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