Sodium Carbonate → HCID 57969705, compound

HRID 384059Notes

Reaction equation

HRID 384059 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[N:15]([C:18]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:16]=[CH:17][C:10]=23)O1.Br[C:39]1[CH:40]=[C:41]([C:45]([CH3:50])([CH2:48][CH3:49])[C:46]#[N:47])[CH:42]=[CH:43][CH:44]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:50][C:45]([C:41]1[CH:40]=[CH:39][CH:44]=[C:43]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[N:15]([C:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:16]=[CH:17][C:10]=23)[CH:42]=1)([CH2:48][CH3:49])[C:46]#[N:47]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 57969632HCID 57969632, compoundHCID 57969821HCID 57969821, compound

Product 1

HCID 57969705HCID 57969705, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine (307 mg, 0.630 mmol), 2-(3-bromophenyl)-2-methylbutanenitrile (150 mg, 0.630 mmol) and 2 M aqueous solution of sodium carbonate (0.945 ml, 1.89 mmol) in dioxane (4 ml) was degassed by vacuum/nitrogen cycles (×5). Bis(tri-tert-butylphosphine)palladium(0) (16.10 mg, 0.032 mmol) was added and the resultant mixture was degassed by vacuum/nitrogen cycles (×5) and stirred at room temperature for 18 hours. The mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium carbonate. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a sticky white solid (0.240 mg, 80% purity, 59% yield).

Workup

  1. customwas degassed by vacuum/nitrogen cycles (×5)
  2. customthe resultant mixture was degassed by vacuum/nitrogen cycles (×5)
  3. customThe mixture was partitioned between ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-7237cdf29058401691e411f524451d43
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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