Sulfuric Acid → (1-(3-Chlorobenzyl)cyclobutyl)(pyridin-2-yl)methanone

HRID 1749150Notes

Reaction equation

HRID 1749150 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[Cl:13][C:14]1[CH:15]=[C:16]([CH:20]([C:22]2([C:26]#N)[CH2:25][CH2:24][CH2:23]2)C)[CH:17]=[CH:18][CH:19]=1.[OH:28]S(O)(=O)=O>C1COCC1>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[CH2:20][C:22]1([C:26]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[O:28])[CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 79732-BromopyridineHCID 66748528HCID 66748528, compoundHCID 178418339Butyllithium

Product 1

HCID 66749362(1-(3-Chlorobenzyl)cyclobutyl)(pyridin-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-bromopyridine (1.1 g, 6.85 mmol) was added n-BuLi (2.7 mL, 6.85 mmol 2.5M in hexane) at −78° C. After stirring for 15 min, a solution of Example 44B (1.0 g, 4.57 mmol) in THF (20 mL) was added. The mixture was stirred at −78° C. for 15 min. followed by slow addition of 9.1 mL of 1 M H2SO4. The mixture was then heated to 50° C. and stirred for 30 min. The aqueous phase was separated and extracted with EtOAc (30 mL).

Workup

  1. stirringThe mixture was stirred at −78° C. for 15 min.
  2. stirringstirred for 30 min
  3. customThe aqueous phase was separated
  4. extractionextracted with EtOAc (30 mL)

Sources & evidence

ORD record
ord-cfcaa85a276444e3907cf517033ec60c
Source dataset
uspto-grants-2015_10
Patent number
US09156788B2

Reaction notes

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