2-Bromo-5-chloropyridine → HCID 178451146, compound

HRID 2207376Notes

Reaction equation

HRID 2207376 reaction equation
[Li]C(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.[C:14]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])[CH2:19][CH2:18]1)(=[O:16])[CH3:15]>C(Cl)Cl>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:14]([C@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])[CH2:19][CH2:18]2)([OH:16])[CH3:15])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 8170982-Bromo-5-chloropyridineHCID 178418306HCID 178418306, compoundHCID 178451155HCID 178451155, compound

Product 1

HCID 178451146HCID 178451146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

t-BuLi (0.950 mL, 1.52 mmol) was added dropwise to a cooled solution of 2-bromo-5-chloropyridine (225 mg, 1.17 mmol) in DCM (11 mL) at −78° C. over 2 minutes. The reaction mixture was stirred for 2 hours at −78° C. and a solution of butyl trans-4-acetylcyclohexanecarboxylate (291 mg, 1.286 mmol) in DCM (1 mL) was added dropwise at −78° C. The reaction mixture was slowly warmed to room temperature over a period of 16 hours. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with DCM (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to afford trans-butyl 4-(1-(5-chloropyridin-2-yl)-1-hydroxyethyl)cyclohexanecarboxylate as a brown oil. MS ESI calc'd for C18H27ClNO3 [M+H]+ 340. found 340.

Workup

  1. temperatureThe reaction mixture was slowly warmed to room temperature over a period of 16 hours
  2. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  3. extractionextracted with DCM (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1084353c6071462ca758614fd7cc31a9
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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