Potassium Carbonate → HCID 15548678, compound

HRID 2262722Notes

Reaction equation

HRID 2262722 reaction equation
[CH2:1]([N:8]([C:22](=[O:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1I)[C:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>[N+](CC)(CC)(CC)CC.[Cl-].CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([N:8]1[C:9]2([CH:10]=[CH:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 15548677HCID 15548677, compound

Product 1

HCID 15548678HCID 15548678, compound

Reagents, catalysts & solvents 3

HCID 5946Tetraethylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of tert-butyl 4-[benzyl(2-iodobenzoyl)amino]-3,6-dihydropyridine-1(2H)-carboxylate (4.63 mmol), Pd(OAc)2 (73 mg, 0.32 mmol, 7 mol %), PPh3 (170 mg, 0.65 mmol, 14 mol %), K2CO3 (959 mg, 6.95 mmol) and Et4NCl (537 mg, 3.24 mmol) in CH3CN (30 ml) is degassed by Argon for 15 min then heated at 110° C. in a sealed tube overnight. Water (40 ml) is added, the layers are separated and the aqueous layer is extracted with EtOAc (40 ml). The combined extracts are washed with brine (40 ml), dried over Na2SO4 and evaporated. The residue is purified by flash column to give the title compound as a light yellow oil.

Workup

  1. customis degassed by Argon for 15 min
  2. additionWater (40 ml) is added
  3. customthe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (40 ml)
  5. washThe combined extracts are washed with brine (40 ml)
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue is purified by flash column

Sources & evidence

ORD record
ord-08e5fdfac4cf4e0aab4a81a09564327d
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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