Sodium Carbonate → HCID 66589203, compound

HRID 1093303Notes

Reaction equation

HRID 1093303 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13](Cl)[N:12]=[C:11]3[N:16]([CH2:19][CH2:20][C:21]#[N:22])[N:17]=[CH:18][C:10]=13)[CH2:2]2.[NH2:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:13]2[N:12]=[C:11]3[N:16]([CH2:19][CH2:20][C:21]#[N:22])[N:17]=[CH:18][C:10]3=[C:9]([N:3]3[CH2:4][CH:5]4[O:8][CH:1]([CH2:7][CH2:6]4)[CH2:2]3)[N:14]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346154-Aminophenylboronic acidHCID 86761507HCID 86761507, compound

Product 1

HCID 66589203HCID 66589203, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

3-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propanenitrile (1.75 mmol) was dissolved in toluene (32 mL) and ethanol (19 mL). 4-Aminophenylboronic acid, pinacol ester (858 mg, 3.9 mmol) was added followed by the addition of a 2M aqueous solution of Na2CO3 (7.1 mL). The mixture was degassed by bubbling a stream of nitrogen through the solution and tetrakis(triphenylphosphine)palladium (53 mg) was added. The mixture was heated under reflux for 4 h, cooled to room temperature and concentrated. The mixture was dissolved in ethyl acetate and washed with brine. The organic phase was dried over MgSO4, filtered and concentrated. The crude product was applied to a silica gel column and eluted with ethyl acetate in hexanes (30-100%) to give 547 mg of the title compound.

Workup

  1. customThe mixture was degassed
  2. customby bubbling a stream of nitrogen through the solution and tetrakis(triphenylphosphine)palladium (53 mg)
  3. additionwas added
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 4 h
  6. concentrationconcentrated
  7. dissolutionThe mixture was dissolved in ethyl acetate
  8. washwashed with brine
  9. dry with materialThe organic phase was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. washeluted with ethyl acetate in hexanes (30-100%)

Sources & evidence

ORD record
ord-fc38b4a592f44345a1b801bd4b63cb05
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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