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

HRID 533118Notes

Reaction equation

HRID 533118 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH2:15]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]([CH: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[CH2:15]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 866748954-(5-Chloro-2,3-dihydrofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 679734534-[5-(4-Methanesulfonylphenyl)-2,3-dihydrofuro[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-(5-chloro-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (400 mg), 4-(methanesulfonyl)phenyl boronic acid (321 mg), aqueous Na2CO3 solution (2 M; 1.60 mL), and dioxane (15 mL) is sparged with argon for 10 min and Pd(PPh3)4 (100 mg) is added. The resulting mixture is heated to 150° C. in a microwave oven until the conversion is complete. The reaction mixture is diluted with water and extracted with ethyl acetate. The organic phase is dried over MgSO4 and the solvent is evaporated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 40:60→20:80) to give the title compound. LC (method 3): tR=1.32 min; Mass spectrum (ESI+): m/z=459 [M+H]+.

Workup

  1. customis sparged with argon for 10 min
  2. additionPd(PPh3)4 (100 mg) is added
  3. additionThe reaction mixture is diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over MgSO4
  6. customthe solvent is evaporated
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 40:60→20:80)

Sources & evidence

ORD record
ord-bfd2447b6df2498d8bcb2b174cce82bc
Source dataset
uspto-grants-2014_10
Patent number
US08853239B2

Reaction notes

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