Cesium carbonate → HCID 131733086, compound

HRID 1518966Notes

Reaction equation

HRID 1518966 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][CH:29]1[CH2:31][CH2:30]1>CN(C=O)C>[CH:29]1([CH2:28][O:1][C:2]2[N:7]=[C:6]([CH:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)[CH:5]=[CH:4][CH:3]=2)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 178451747HCID 178451747, compound

Product 1

HCID 131733086HCID 131733086, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

Stir tert-butyl 4-(6-hydroxypyridin-2-yl)piperidine-1-carboxylate (0.25 g, 0.90 mmol) in DMF (10 mL) and add cesium carbonate (0.44 g, 1.35 mmol) and (bromomethyl)cyclopropane (0.13 g, 0.99 mmol). Heat the mixture to 30° C. and stir overnight. Quench the reaction with water, and extract three times with EtOAc (20 mL). Combine the organic extracts. Wash the extracts with water then brine; dry over sodium sulphate; collect the filtrate; and concentrate under vacuum to give the crude product. Purify using silica gel normal phase flash column chromatography using a gradient of 0-30% ethyl acetate in petroleum ether to give the title compound (0.28 g, 94%) as a clear oil. MS (m/z): 333 (M+1).

Workup

  1. customQuench
  2. customthe reaction with water
  3. extractionextract three times with EtOAc (20 mL)
  4. washWash the extracts with water
  5. dry with materialdry over sodium sulphate
  6. customcollect the filtrate
  7. concentrationand concentrate under vacuum
  8. customto give the crude product
  9. customPurify

Sources & evidence

ORD record
ord-e3ee014383f04c61987574c8e9ce089c
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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