Water → [7-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl]-methanol hydrochloride

HRID 1445077Notes

Reaction equation

HRID 1445077 reaction equation
[BH4-].[Na+].[ClH:3].[CH2:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]1[C:14]1[N:15]=[CH:16][CH:17]=[C:18]2[C:22]([CH:23]=[O:24])=[C:21]([CH3:25])[N:20]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[C:19]=12.O>CO>[ClH:3].[CH2:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]1[C:14]1[N:15]=[CH:16][CH:17]=[C:18]2[C:22]([CH2:23][OH:24])=[C:21]([CH3:25])[N:20]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[C:19]=12

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 866152557-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-3-carbaldehyde hydrochloride

Product 1

HCID 67142464[7-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl]-methanol hydrochlorideYield 31.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (4.7 mg, 0.124 mmol) was added to a solution of 7-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-3-carbaldehyde hydrochloride (25 mg) prepared in Example 616 in methanol (2 ml). The reaction mixture was stirred for 1 hour and water was added thereto. The reaction mixture was extracted with ethyl acetate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 8 mg of the titled compound as a white solid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1
  4. dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  5. filtrationfiltered

Sources & evidence

ORD record
ord-9755b8e325c34caf97a4d7fd5c2e14e5
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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