HCID 86686203, compound → HCID 86686228, compound

HRID 1021269Notes

Reaction equation

HRID 1021269 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([F:28])=[C:12]([N:16]2[CH2:21][CH:20]=[C:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:18][CH2:17]2)[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[C].[Pd].CCO>[Si:1]([O:8][CH2:9][C:10]1[C:11]([F:28])=[C:12]([N:16]2[CH2:17][CH2:18][CH:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][CH2:21]2)[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86686203HCID 86686203, compound

Product 1

HCID 86686228HCID 86686228, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1′-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-1′,2′,3′,6′-tetrahydro-3,4′-bipyridine (257 mg) was mixed with EtOH (5 ml), and 10% palladium carbon (55 mg) was added thereto under argon atmosphere, followed by stirring at room temperature overnight under hydrogen atmosphere. The reaction mixture was filtered using Celite as a filtration adjuvant, and the filtrate was concentrated under reduced pressure to obtain 3-{1-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]piperidin-4-yl}pyridine (239 mg).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3208db5a0b1941299b6e68171bb45de9
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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