Dichloromethane → HCID 86686203, compound

HRID 1021228Notes

Reaction equation

HRID 1021228 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([F:29])=[C:12]([N:16]2[CH2:21][CH2:20][C:19]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)(O)[CH2:18][CH2:17]2)[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClCCl.CS(Cl)(=O)=O>CN(C1C=CN=CC=1)C.O>[Si:1]([O:8][CH2:9][C:10]1[C:11]([F:29])=[C:12]([N:16]2[CH2:17][CH:18]=[C:19]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=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

6

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 86686204HCID 86686204, compound

Product 1

HCID 86686203HCID 86686203, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

1-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-4-(pyridin-3-yl)piperidin-4-ol (908 mg) was mixed with dichloromethane (15 ml), and TEA (1.1 g), DMAP (799 mg), and MsCl (749 mg) were added thereto at 0° C., followed by stirring at room temperature overnight. Water and EtAOc were added to the reaction mixture, and the organic layer was washed with water and saturated brine, and dried over anhydrous sodium carbonate. The solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane) to obtain 1′-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-1′,2′,3′,6′-tetrahydro-3,4′-bipyridine (477 mg).

Workup

  1. additionwere added
  2. customat 0° C.
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium carbonate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-5ccfe91bacf7469481fdd2b84c18cbe4
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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