Potassium Carbonate → HCID 21906609, compound

HRID 1247103Notes

Reaction equation

HRID 1247103 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][C:18]=2I)=[O:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:28]([O-])([O-])=[O:29].[K+].[K+]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][C:28](=[O:29])[C:18]3[CH:19]=[C:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=[CH:22][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 21906404HCID 21906404, compound

Product 1

HCID 21906609HCID 21906609, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To a stirring solution of 2-[(1-Boc-piperidin-4-ylcarbonyl)amino]-5-methylsulfonyliodobenzene (1.89 g, 3.72 mmol) in acetonitrile (50 mL) was added K2CO3 (2.53 g, 18.6 mmol) followed by Pd(PPh3)4 (0.22 g, 0.19 mmol) and CuI (0.036 g, 0.19 mmol). The mixture was placed under an atmosphere of CO and heated to 75° C. After 2 h, the heat was removed and the mixture was diluted with ethyl acetate and washed with water, then brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo. The residue was chromatographed over silica gel, eluting with a gradient of 10% to 20% ethyl acetate in dichloromethane. The product containing fractions were combined and concentrated in vacuo to give 0.485 g (32%) of a white solid.

Workup

  1. customthe heat was removed
  2. additionthe mixture was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic phase was then dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed over silica gel
  8. washeluting with a gradient of 10% to 20% ethyl acetate in dichloromethane
  9. additionThe product containing fractions
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-257cf189c6f44a369fdf9d7ef509f7e0
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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