Dichloromethane → HCID 118038136, compound

HRID 2272492Notes

Reaction equation

HRID 2272492 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[C:11](=[O:28])[C:10]=1I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30](N(CC)CC)[CH3:31].ClCCl>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[C:11](=[O:28])[C:10]=1[CH:30]=[CH2:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 118037682HCID 118037682, compound

Product 1

HCID 118038136HCID 118038136, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 4-(4-(benzyloxy)-3-iodo-2-oxopyridin-1(2H)-yl)piperidine-1-carboxylate (2.4 g), potassium vinyl trifluoroborate (0.945 g), triethylamine (1.3 mL), a dichloromethane adduct of 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (0.269 g), and ethanol (47 mL) was stirred overnight at 90 C in a nitrogen atmosphere. After cooling to room temperature, the solvent was distilled off under reduced pressure. Water and ethyl acetate were added to the obtained residue, and the organic layer was separated. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to obtain the title compound (1.48 g).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater and ethyl acetate were added to the obtained residue
  3. customthe organic layer was separated
  4. washThe obtained organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-aa74238b89a5430ca43956c7ebe26ab5
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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