Sodium Carbonate → 4-[5-(4-Methanesulfonylphenyl)furo[2,3-c]pyridin-2-yl]piperidine-1-carboxylic acid tert-butyl ester

HRID 1622227Notes

Reaction equation

HRID 1622227 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][S:25]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)(=[O:27])=[O:26].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20]([C:31]4[CH:32]=[CH:33][C:28]([S:25]([CH3:24])(=[O:27])=[O:26])=[CH:29][CH:30]=4)[CH:21]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 866748894-(5-Chlorofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 679736224-[5-(4-Methanesulfonylphenyl)furo[2,3-c]pyridin-2-yl]piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 4-(5-chloro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (390 mg), 4-(methanesulfonyl)phenyl boronic acid (350 mg), aqueous Na2CO3 solution (2 M; 1.50 mL), and dioxane (10 mL) is sparged with argon for 10 min and Pd(PPh3)4 (100 mg) is added. The resulting mixture is heated to 170° C. in a microwave oven until the conversion is complete. The reaction mixture is concentrated in vacuo, diluted with water and extracted with ethyl acetate. The organic phase is washed with brine, dried over MgSO4, and the solvent is evaporated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 60:40→40:60) to give the title compound. LC (method 5): tR=1.32 min; Mass spectrum (ESI+): m/z=457 [M+H]+.

Workup

  1. customis sparged with argon for 10 min
  2. additionPd(PPh3)4 (100 mg) is added
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with brine
  7. dry with materialdried over MgSO4
  8. customthe solvent is evaporated
  9. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 60:40→40:60)

Sources & evidence

ORD record
ord-f710b6c9d30c42fea0754f587262c7d4
Source dataset
uspto-grants-2014_07
Patent number
US08778926B2

Reaction notes

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