(Bis(2-methoxyethyl)amino)sulfur trifluoride → 5-(2-Fluoro-4-methanesulfonyl-phenyl)-2-[1-(2-fluoro-2-methyl-propyl)-piperidin-4-yl]-furo[2,3-c]pyridine

HRID 1471790Notes

Reaction equation

HRID 1471790 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[F:14][C:15]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:16]=1[C:25]1[CH:26]=[C:27]2[CH:33]=[C:32]([CH:34]3[CH2:39][CH2:38][N:37]([CH2:40][C:41](O)([CH3:43])[CH3:42])[CH2:36][CH2:35]3)[O:31][C:28]2=[CH:29][N:30]=1>ClCCl.CO>[F:14][C:15]1[CH:20]=[C:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:18]=[CH:17][C:16]=1[C:25]1[CH:26]=[C:27]2[CH:33]=[C:32]([CH:34]3[CH2:35][CH2:36][N:37]([CH2:40][C:41]([F:11])([CH3:43])[CH3:42])[CH2:38][CH2:39]3)[O:31][C:28]2=[CH:29][N:30]=1

Participants

5

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 866945785-(2-Fluoro-4-methanesulfonyl-phenyl)-2-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-furo[2,3-c]pyridine

Product 1

HCID 717367225-(2-Fluoro-4-methanesulfonyl-phenyl)-2-[1-(2-fluoro-2-methyl-propyl)-piperidin-4-yl]-furo[2,3-c]pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Bis(2-methoxyethyl)aminosulfur trifluoride (50% in toluene; 0.27 mL) is added to a solution of 5-(2-fluoro-4-methanesulfonyl-phenyl)-2-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-furo[2,3-c]pyridine (0.19 g) in dichloromethane (3 mL) chilled in an ice bath. The solution is stirred at room temperature overnight. The solution is diluted with dichloromethane and little methanol and washed with aqueous NaHCO3 solution. The solution is dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→1:2) to give the title compound. LC (method 4): tR=1.09 min; Mass spectrum (ESI+): m/z=449 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. washwashed with aqueous NaHCO3 solution
  3. dry with materialThe solution is dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:1→1:2)

Sources & evidence

ORD record
ord-2dd7d25333fe46d39b35435421cfce5b
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

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