2-Bromo-5-(methylsulfonyl)pyridine → HCID 66935329, compound

HRID 1798798Notes

Reaction equation

HRID 1798798 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][OH:19])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][N:22]=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@@H:14]3[CH2:16][C@@H:15]3[CH2:17][CH2:18][O:19][C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][N:22]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 98994832-Bromo-5-(methylsulfonyl)pyridineHCID 581286112-{(1S,2R)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanol

Product 1

HCID 66935329HCID 66935329, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

rac-cis-2-{2-[1-(5-Chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanol from step 2 of example 6 (338 mg, 1.2 mmol) was dissolved in DMF (0.7 ml, 0.38 M). Nat (60% in oil, 144 mg, 3.6 mmol) was added and the mixture was stirred for 10 min at RT. 2-Bromo-5-(methylsulfonyl)pyridine (340 mg, 1.44 mmol) was added and the mixture stirred at RT 2½ hours. The mixture was diluted with 75 ml water and extracted with iPrOAc (3×50 ml), adding brine to break the layers. Organic phases were combined, washed with brine, dried over Na2SO4, filtered and stripped. The product was purified by chromatography on SiO2 (40 g) eluting with 40% EtOAc:Hexanes.

Workup

  1. additionNat (60% in oil, 144 mg, 3.6 mmol) was added
  2. stirringthe mixture stirred at RT 2½ hours
  3. extractionextracted with iPrOAc (3×50 ml)
  4. additionadding brine
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customThe product was purified by chromatography on SiO2 (40 g)
  9. washeluting with 40% EtOAc

Sources & evidence

ORD record
ord-37ce4e66169945e5969dd39805050e92
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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