Cesium carbonate → HCID 118048098, compound

HRID 715555Notes

Reaction equation

HRID 715555 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[Br:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 115221-Bromo-4-iodobenzeneHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 118048098HCID 118048098, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

tert-Butyl piperidin-4-ylcarbamate (500 mg), 1-bromo-4-iodobenzene (710 mg) and Cs2CO3 (1.2 g) are dissolved in 1,4-dioxane (15 mL) and purged for 10 minutes with argon. 4,5-Bis-(diphenylphosphino)-9,9-dimethylxanthen (Xantphos, 115 mg) and tris-(dibenzylideneacetone)-dipalladium-(0) (Pd2(dba)3, 45 mg) are added and the mixture is heated for 12 hours at 110° C. Then the mixture is partitioned between saturated aqueous NH4Cl solution and ethylacetate and the organic phase is washed with brine and dried (MgSO4). The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30) to give the title compound. LC (method 2): tR=1.14 min; Mass spectrum (ESI+): m/z=355 [M+H]+.

Workup

  1. custompurged for 10 minutes with argon
  2. addition4,5-Bis-(diphenylphosphino)-9,9-dimethylxanthen (Xantphos, 115 mg) and tris-(dibenzylideneacetone)-dipalladium-(0) (Pd2(dba)3, 45 mg) are added
  3. customThen the mixture is partitioned between saturated aqueous NH4Cl solution and ethylacetate
  4. washthe organic phase is washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvents are evaporated in vacuo
  7. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30)

Sources & evidence

ORD record
ord-b7aed381efdc4542b34b43e802e5d03e
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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