Dichloromethane → HCID 89500542, compound

HRID 2178515Notes

Reaction equation

HRID 2178515 reaction equation
CC(C)([O-])C.[K+].[CH:7]1([OH:11])[CH2:10][CH2:9][CH2:8]1.Cl.F[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]2[CH2:24][CH2:23][NH:22][CH2:21]2)[N:15]=1.ClCCl>CS(C)=O.O>[CH:7]1([O:11][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]3[CH2:24][CH2:23][NH:22][CH2:21]3)[N:15]=2)[CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 76218CyclobutanolHCID 23665647Potassium tert-butoxideHCID 89500387HCID 89500387, compound

Product 1

HCID 89500542HCID 89500542, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

Potassium tert-butoxide (337 mg, 3 mmol, 3 eq) is added portionwise at room temperature to a solution of cyclobutanol (144 mg, 2 mmol, 2 eq) in DMSO (2 ml) and the mixture is stirred for 2 days. 2-Fluoro-6-(pyrrolidin-3-yl)pyridine hydrochloride (202 mg, 1 mmol, 1 eq) in DMSO (2 ml) is added and the mixture is stirred for 48 hours. Dichloromethane and water are then added to the reaction mixture, and the two phases are separated after vigorous shaking. The aqueous layer is reextracted with dichloromethane. The combined organic layers are dried on MgSO4, filtered and the filtrate condensed under reduced pressure to afford crude 2-(cyclobutyloxy)-6-(pyrrolidin-3-yl)pyridine a1-72, which is used in the next step without any further purification.

Workup

  1. stirringthe mixture is stirred for 48 hours
  2. customthe two phases are separated after vigorous shaking
  3. customThe combined organic layers are dried on MgSO4
  4. filtrationfiltered
  5. customthe filtrate condensed under reduced pressure

Sources & evidence

ORD record
ord-d2a265d2ee574a03a042b4d21322e25e
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

Loading…