Sodium Bicarbonate → HCID 23156893, compound

HRID 1098311Notes

Reaction equation

HRID 1098311 reaction equation
ClCCl.B(Br)(Br)Br.[OH:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[C:20]([C:26]4[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][C:27]=4[CH3:34])[NH:21][C:22]3=[O:25])=[CH:17][CH:16]=2)[CH2:10]1.C(=O)(O)[O-].[Na+]>ClCCl>[OH:32][C:29]1[CH:30]=[CH:31][C:26]([C:20]2[NH:21][C:22](=[O:25])[C:23]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[C:15]([N:11]2[CH2:12][CH2:13][CH2:14][CH:9]([OH:8])[CH2:10]2)[CH:24]=3)=[C:27]([CH3:34])[CH:28]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 23156797HCID 23156797, compound

Product 1

HCID 23156893HCID 23156893, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.070 ml (0.070 mmol) of a 1 M boron tribromide dichloromethane solution was added at 0° C. to a dichloromethane solution (0.5 ml) containing 17 mg (0.0466 mmol) of the 7-(3-hydroxypiperidin-1-yl)-3-(4-methoxy-2-methylphenyl)-2H-isoquinolin-1-one obtained in Example 90. The obtained mixture was stirred at the same above temperature for 30 minutes. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, and the mixture was then extracted with dichloromethane/methanol (5:1). The extract was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1 to 10:1), so as to obtain 10 mg (61%) of 3-(4-hydroxy-2-methylphenyl)-7-(3-hydroxypiperidin-1-yl)-2H-isoquinolin-1-one in the form of a light brown solid.

Workup

  1. extractionthe mixture was then extracted with dichloromethane/methanol (5:1)
  2. concentrationThe extract was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1 to 10:1)

Sources & evidence

ORD record
ord-09406d6096ec44078f859491d0c681c3
Source dataset
uspto-grants-2012_03
Patent number
US08143274B2

Reaction notes

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