Sodium Carbonate → HCID 44178192, compound

HRID 1890422Notes

Reaction equation

HRID 1890422 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([NH:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[C:10]2=[N:23][C:24]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][N:29]=3)=[CH:25][C:26](=[O:27])[N:9]2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:34][N:35]1[CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH:37]=[N:36]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([NH:13][C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([C:38]3[CH:37]=[N:36][N:35]([CH3:34])[CH:39]=3)=[CH:17][CH:16]=2)[C:10]2=[N:23][C:24]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][N:29]=3)=[CH:25][C:26](=[O:27])[N:9]2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium Carbonate2×HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 44177962HCID 44177962, compound

Product 1

HCID 44178192HCID 44178192, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture containing 0.145 g (0.28 mmol) of 9-(4-bromo-benzoylamino)-4-oxo-2-pyrimidin-4-yl-5,6,8,9-tetrahydro-4H-1,4a,7-triaza-benzocycloheptene-7-carboxylic acid ethyl ester (example 10), 0.082 g (0.40 mmol) of 1-methyl-1H-pyrazole-4-boronic acid pinacol ester, 0.35 mL (0.71 mmol) of sodium carbonate (solution 2M), 0.065 g (0.06 mmol) of tetrakis(tri-phenylphosphine)palladium in 5.60 mL of toluene/EtOH (10/1) under argon atmosphere was stirred at 90° C. for 15 hours. The reaction mixture was cooled, aqueous saturated solution of sodium carbonate was added and the resulting solution extracted with dichloromethane. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 98/2/0.2 to 97/3/0.3 to afford 0.088 g (76%) of the pure product as a white powder.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe resulting solution extracted with dichloromethane
  3. washThe combined extracts were washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude product was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol/aqueous ammonia solution (29%) in the proportions 98/2/0.2 to 97/3/0.3

Sources & evidence

ORD record
ord-bf0f56965e0e4b6e8c7d58be4156114b
Source dataset
uspto-grants-2013_08
Patent number
US08507476B2

Reaction notes

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