HCID 22038501, compound → HCID 17955253, compound

HRID 1790030Notes

Reaction equation

HRID 1790030 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2[N:14]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:16][C:10]=2[CH2:9]1)C1C=CC=CC=1>CO.O1CCCC1.[OH-].[OH-].[Pd+2]>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]2[N:14]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:31])[C:11]3[CH2:12][CH2:13][NH:8][CH2:9][C:10]=3[CH:16]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 1

HCID 22038501HCID 22038501, compound

Product 1

HCID 17955253HCID 17955253, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Benzyl-2-(4-methoxyphenyl)-1-(2-methylphenyl)4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (5.6 g, 14 mmol; prepared by methods as described in Example 1) was added to a suspension of palladium hydroxide on carbon (20%, 1.52 g, 2 mmol) in dry methanol (130 mL) and tetrahydrofuran (100 mL) under argon. The mixture was degassed by vacuum, and purged by argon several times. Then, the flask was fitted with a balloon containing hydrogen gas, and the mixture was stirred under H2 at rt overnight. The reaction mixture was filtered through Celite, and the filtrate evaporated to provide the product (4.3 g, 98%). LC-MS m/z (MH+) 409.2, retention time 2.30 min (method 2).

Workup

  1. customThe mixture was degassed by vacuum
  2. custompurged by argon several times
  3. customThen, the flask was fitted with a balloon
  4. additioncontaining hydrogen gas
  5. filtrationThe reaction mixture was filtered through Celite
  6. customthe filtrate evaporated

Sources & evidence

ORD record
ord-a0ec281597b743318293b3929a95087b
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

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