Water → HCID 67142101, compound

HRID 1932401Notes

Reaction equation

HRID 1932401 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[N:12]=[C:13]([CH:30]=O)[CH:14]=[C:15]2[C:19]([CH3:20])=[C:18]([CH3:21])[N:17]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[C:16]=12.[Cl:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][NH2:37].[BH4-].[Na+].O>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[C:11]1[N:12]=[C:13]([CH2:30][NH:37][CH2:36][C:35]2[CH:38]=[CH:39][CH:40]=[C:33]([Cl:32])[CH:34]=2)[CH:14]=[C:15]2[C:19]([CH3:20])=[C:18]([CH3:21])[N:17]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)[C:16]=12

Participants

7

Reactant 4

HCID 962WaterHCID 77802Benzenemethanamine, 3-chloro-HCID 4311764Sodium borohydrideHCID 86615265HCID 86615265, compound

Product 1

HCID 67142101HCID 67142101, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 7-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-fluorobenzyl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbaldehyde (30 mg, 0.07 mmol) prepared in Step 1 of Example 864 and 3-chlorobenzylamine (9.75 μl, 0.08 mmol) in methanol (3 ml) was refluxed for 3 hours. Titanium(IV) isopropoxide (40 μl) and sodium borohydride (5.49 mg, 0.15 mmol) were added at room temperature to the reaction mixture, which was then stirred overnight. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5, v/v) to give 21.7 mg of the titled compound as a white solid.

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5

Sources & evidence

ORD record
ord-fc6fdaaa90ff43b2833b0e236315ea2c
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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