Sodium Carbonate → HCID 71093731, compound

HRID 1409693Notes

Reaction equation

HRID 1409693 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([N:20]([C:24]([C:26]2[CH:27]=[N:28][C:29](Br)=[CH:30][CH:31]=2)=[O:25])[CH:21]2[CH2:23][CH2:22]2)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[CH3:33][S:34]([C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1)(=[O:36])=[O:35]>CN(C)C=O>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([N:20]([CH:21]2[CH2:23][CH2:22]2)[C:24]([C:26]2[CH:27]=[N:28][C:29]([C:40]3[CH:41]=[CH:42][C:37]([S:34]([CH3:33])(=[O:36])=[O:35])=[CH:38][CH:39]=3)=[CH:30][CH:31]=2)=[O:25])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 86686153HCID 86686153, compound

Product 1

HCID 71093731HCID 71093731, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2 M aqueous Na2CO3 solution (8.26 mL) is added to a mixture of 4-[(6-bromo-pyridine-3-carbonyl)-cyclopropyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (500 mg) and 4-(methanesulfonyl)phenylboronic acid (259 mg) in N,N-dimethylformamide (5 mL). The mixture is sparged with argon for 10 min and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium dichloromethane complex (96 mg) is added. The resulting mixture is stirred for 6 h at 90° C. After cooling to room temperature, water (50 mL) is added and the aqueous phase is extracted with ethyl acetate. The organic phase is dried over MgSO4, the solvent is evaporated, and the residue is chromatographed on silica gel (ethyl acetate/cyclohexane 3:1→1:0) to afford the title compound. LC (method 6): tR=1.17 min; Mass spectrum (ESI+): m/z=500 [M+H]+.

Workup

  1. customThe mixture is sparged with argon for 10 min
  2. addition[1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium dichloromethane complex (96 mg) is added
  3. temperatureAfter cooling to room temperature
  4. additionwater (50 mL) is added
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. dry with materialThe organic phase is dried over MgSO4
  7. customthe solvent is evaporated
  8. customthe residue is chromatographed on silica gel (ethyl acetate/cyclohexane 3:1→1:0)

Sources & evidence

ORD record
ord-55579dd5f880457a9694cf226c8b95aa
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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