Cesium carbonate → HCID 66579030, compound

HRID 1521878Notes

Reaction equation

HRID 1521878 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH2:31][O:32][CH3:33])[C:12]1[C:13]([C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:24])=[N:14][N:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=1)(=[O:10])=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:33][O:32][CH2:31][N:11]1[C:12]2[C:13]([C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])=[N:14][N:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:16]=2[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]1(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 66580218HCID 66580218, compound

Product 1

HCID 66579030HCID 66579030, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A mixture of 2-bromo-N-(methoxymethyl)-N-[3(morpholin-4-ylcarbonyl)-1-phenyl-1H-pyrazol -4-yl] benzenesulfonamide (240 mg; 0.45 mmol; 1.00 eq.), palladium acetate (20 mg; 0.09 mmol; 0.20 eq.), triphenylphosphine (94 mg; 0.36 mmol; 0.80 eq.) and Cs2CO3 (584 mg; 1.79 mmol; 4.00 eq.) is flushed with N2 for 10 minutes. Toluene (50 mL) is added and the resulting mixture is stirred at reflux for 2 hours. After this time, reaction mixture is filtered through a short plug of celite, ished with ethyl acetate. Combined organic phase are ished with NaHCO3 then brine, dried over sodium sulfate and concentrated in vacuo and purified by flash chromatography to give the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 8.03 (dd, J=1.3, 7.5 Hz, 1H), 7.88-7.46 (m, 7H), 7.04-6.94 (m, 1H), 5.15 (s, 2H), 3.69 (s, 6H), 3.64-3.54 (m, 2H), 2.89 (s, 3H). HPLC (max plot) 83.4%; Rt 3.71 min. MS (ESI+) 423.2.

Workup

  1. customis flushed with N2 for 10 minutes
  2. additionToluene (50 mL) is added
  3. temperatureat reflux for 2 hours
  4. customAfter this time, reaction mixture
  5. filtrationis filtered through a short plug of celite
  6. dry with materialbrine, dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-cd6a1680ce1841818a22975ef442b0c8
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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