Sodium Carbonate → HCID 42635383, compound

HRID 384064Notes

Reaction equation

HRID 384064 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][CH2:14][C:15]3=[O:18])=[CH:11][CH:10]=2)O1.I[C:21]1[CH:26]=[CH:25][N:24]=[C:23]2[NH:27][N:28]=[CH:29][C:22]=12.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O>[NH:27]1[C:23]2=[N:24][CH:25]=[CH:26][C:21]([C:9]3[CH:17]=[C:16]4[C:12]([CH2:13][CH2:14][C:15]4=[O:18])=[CH:11][CH:10]=3)=[C:22]2[CH:29]=[N:28]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 177500786-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-oneHCID 576428014-Iodo-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 42635383HCID 42635383, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one (3 g, 11.6 mmol) and 4-iodo-1H-pyrazolo[3,4-b]pyridine (3.13 g, 12.8 mmol) in DME (20 mL) was added aq. sodium carbonate (2M, 11.62 mL, 23.2 mmol) followed by tetrakistriphenylphosphine palladium (978 mg, 0.846 mmol). The mixture was microwaved for 90 min at 150° C. The reaction mixture was diluted with ethyl acetate and water and the layers separated. The organic layer was filtered off since it contained a yellow precipitate (desired prod ca. 85% pure) and then it was washed with water and then dried (MgSO4), filtered and concentrated and added to the precipitate above. The solids were recrystallised from boiling MeOH-TRF to provide the pure ketone (1.62 g, 56%) as a yellow solid.

Workup

  1. customThe mixture was microwaved for 90 min at 150° C
  2. customthe layers separated
  3. filtrationThe organic layer was filtered off since it
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionadded to the precipitate above
  9. customThe solids were recrystallised

Sources & evidence

ORD record
ord-fc860534451b4cb29cad95bf2afbfb2c
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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