Sodium Carbonate → HCID 68778513, compound

HRID 2261259Notes

Reaction equation

HRID 2261259 reaction equation
Br[C:2]1[C:7](=[O:8])[N:6]([CH3:9])[C:5]2[N:10]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[N:11]=[CH:12][C:4]=2[CH:3]=1.C([O:24][CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=[O:31])=[CH:28][C:27]=1B1OC(C)(C)C(C)(C)O1)(=O)C.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>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.CCOC(C)=O>[F:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([F:19])[C:13]=1[N:10]1[C:5]2[N:6]([CH3:9])[C:7](=[O:8])[C:2]([C:35]3[CH:34]=[C:29]([CH:28]=[CH:27][C:26]=3[CH2:25][OH:24])[C:30]([OH:32])=[O:31])=[CH:3][C:4]=2[CH:12]=[N:11]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 46197691HCID 46197691, compoundHCID 57543437HCID 57543437, compound

Product 1

HCID 68778513HCID 68778513, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (38 mg, 33 μmol), 5-bromo-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (373 mg, 1096 μmol), methyl 4-(acetoxymethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (403 mg, 1206 μmol) were treated with 1,4-dioxane (5.4 mL) and 1 M aqueous Na2CO3 (2.74 mL, 2741 μmol) under argon and heated in a microwave at 130° C. for 30 min. The reaction mixture was treated with EtOAc (20 mL) and extracted with 1N NaOH (2×15 mL). The pH was adjusted to ca. pH 6 with 5N HCl and extracted with DCM (3×20 mL), dried over MgSO4, filtered and concentrated affording the title compound (186 mg) as a yellow tar. The crude residue was used in the next step without further purification. MS (ESI, pos.ion) m/z: 412.1 (M+1).

Workup

  1. extractionextracted with 1N NaOH (2×15 mL)
  2. extractionextracted with DCM (3×20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ff229d560dbd4a29bcc281cf793c578a
Source dataset
uspto-grants-2010_12
Patent number
US07846944B2

Reaction notes

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