Sodium Carbonate → HCID 72194734, compound

HRID 2406337Notes

Reaction equation

HRID 2406337 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Cl[C:8]1[CH:9]=[C:10]2[CH2:31][C:15]3([CH2:30][C:17]4([CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)[CH2:16]3)[O:14][C:11]2=[CH:12][N:13]=1.[CH3:32][S:33]([C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1)(=[O:35])=[O:34].O1CCOCC1>CO>[CH3:32][S:33]([C:36]1[CH:41]=[CH:40][C:39]([C:8]2[CH:9]=[C:10]3[CH2:31][C:15]4([CH2:30][C:17]5([CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:21][CH2:22]5)[CH2:16]4)[O:14][C:11]3=[CH:12][N:13]=2)=[CH:38][CH:37]=1)(=[O:35])=[O:34]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 867012005-Chloro-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Product 1

HCID 72194734HCID 72194734, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 M aqueous Na2CO3 solution (0.30 mL) is added to a mixture of 5-chloro-1″-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (0.10 g), 4-(methanesulfonyl)phenylboronic acid (0.08 g), 1,4-dioxane (1.5 mL), and methanol (0.5 mL) at room temperature. The mixture is sparged with Ar for 10 min prior to addition of PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (20 mg). The resulting mixture is heated to reflux temperature and stirred at this temperature for 2 h. After cooling to room temperature, water and methanol are added and the resulting mixture is filtered. The filtrate is concentrated and the residue is chromatographed on reversed phase (HPLC, methanol/water) to give the title compound. LC (method 2): tR=1.72 min; Mass spectrum (ESI+): m/z=485 [M+H]+.

Workup

  1. customThe mixture is sparged with Ar for 10 min
  2. additionto addition of PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (20 mg)
  3. temperatureThe resulting mixture is heated
  4. temperatureto reflux temperature
  5. additionwater and methanol are added
  6. filtrationthe resulting mixture is filtered
  7. concentrationThe filtrate is concentrated
  8. customthe residue is chromatographed on reversed phase (HPLC, methanol/water)

Sources & evidence

ORD record
ord-17ae929aaa98458d83bda0629f4d58b2
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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