Sodium Carbonate → HCID 57474957, compound

HRID 1929401Notes

Reaction equation

HRID 1929401 reaction equation
[C:1]1([N:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:8]([C:10]2[C:14](Br)=[CH:13][N:12]([C:16]34[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]5)[CH2:17]3)[CH2:23]4)[N:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1B(O)O)=[O:33].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C.O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]12([N:12]3[CH:13]=[C:14]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[CH:32]=[O:33])[C:10]([C:8]([N:7]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[O:9])=[N:11]3)[CH2:17][CH:18]3[CH2:19][CH:20]([CH2:21][CH:22]([CH2:24]3)[CH2:23]1)[CH2:25]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 4070345HCID 4070345, compound

Product 1

HCID 57474957HCID 57474957, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
180 °C

Procedure

1-Adamantan-1-yl-4-bromo-1H-pyrazole-3-carboxylic acid diphenylamide (47 mg), 2-formylphenylboronic acid (18 mg), sodium carbonate (32 mg), and tetrakis(triphenylphosphine)palladium(0) (7 mg) were combined in dimethoxyethane/ethanol/water 12/3/4 (1 mL) and heated in a CEM Discover microwave reactor at 180° C. for 5 minutes. The reaction was cooled, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration and concentration, the crude material was purified by column chromatography on silica gel using hexanes/ethyl acetate 4/1.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-45aa0e0a608742358000d526fc743990
Source dataset
uspto-grants-2012_05
Patent number
US08188077B2

Reaction notes

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