Sodium Carbonate → HCID 67973481, compound

HRID 1184695Notes

Reaction equation

HRID 1184695 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:22][C:21]3[C:16](=[N:17][C:18](Cl)=[CH:19][CH:20]=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:22][C:21]3[C:16](=[N:17][C:18]([C:31]4[CH:32]=[CH:33][C:28]([S:25]([CH3:24])(=[O:27])=[O:26])=[CH:29][CH:30]=4)=[CH:19][CH:20]=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 86674888HCID 86674888, compound

Product 1

HCID 67973481HCID 67973481, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 4-(5-chloro-furo[3,2-b]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (50 mg) and 4-(methanesulfonyl)phenyl boronic acid (45 mg) in [1,4]dioxane (1.5 mL) in a microwave oven suited vessel charged with a stir bar a 2 M aqueous Na2CO3 solution (1904) is added. The mixture is sparged with argon for 10 min and Pd(PPh3)4 (21 mg) is added. The vessel is capped and the mixture is stirred under microwave irradiation at 140° C. for 35 min. After cooling the mixture to room temperature, dichloromethane and water are added. The organic phase is washed with brine, dried (MgSO4) and the solvent is evaporated. The crude product is purified by HPLC on reversed phase (MeOH/H2O/TFA). Yield: 25 mg (37% of theory); LC (method 2): tR=1.36 min; Mass spectrum (ESI+): m/z=457 [M+H]+.

Workup

  1. additionis added
  2. customThe mixture is sparged with argon for 10 min
  3. additionPd(PPh3)4 (21 mg) is added
  4. customThe vessel is capped
  5. temperatureAfter cooling the mixture to room temperature
  6. additiondichloromethane and water are added
  7. washThe organic phase is washed with brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent is evaporated
  10. customThe crude product is purified by HPLC on reversed phase (MeOH/H2O/TFA)

Sources & evidence

ORD record
ord-e5bbde75b6d24790ab2604b205752bd0
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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