Potassium Carbonate → HCID 58897002, compound

HRID 1409118Notes

Reaction equation

HRID 1409118 reaction equation
BrC1C([Cl:8])=CN=C2NC=CC=12.[C:12]1([CH3:38])[CH:17]=[CH:16][C:15]([S:18]([N:21]2[C:25]3=[N:26][CH:27]=[CH:28][C:29]([C:30]4[CH:31]=[C:32]([CH2:36]O)[CH:33]=[CH:34][CH:35]=4)=[C:24]3[CH:23]=[CH:22]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].O>[Cl:8][CH2:36][C:32]1[CH:31]=[C:30]([C:29]2[CH:28]=[CH:27][N:26]=[C:25]3[N:21]([S:18]([C:15]4[CH:16]=[CH:17][C:12]([CH3:38])=[CH:13][CH:14]=4)(=[O:20])=[O:19])[CH:22]=[CH:23][C:24]=23)[CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 468355224-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridineHCID 58896939HCID 58896939, compound

Product 1

HCID 58897002HCID 58897002, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 11979704Tetrakis(triphenylphosphine)palladiumSolvent

Procedure

Under N2, Compound D (1.95 g, 8.49 mmol) and compound G′ (1.1 equivalent, 9.34 mmol) and K2CO3 (3.3 equivalent, 28 mmol) were dissolved into 9 mL of dioxane and 3 mL of H2O in a microwave, to this reaction mixture, catalytic amount of Pd(Pph3)4 was added and the tube was under microwave irradiation at 170° C. for 10 min. After cooled down the reaction mixture, the product crashed out and filtered off the solid, washed with H2O and CH3CN respectively to obtain title compound H′ quantitatively. MS+1=430.5.

Workup

  1. additionwas added
  2. customthe tube was under microwave irradiation at 170° C. for 10 min
  3. temperatureAfter cooled down the reaction mixture
  4. filtrationfiltered off the solid
  5. washwashed with H2O and CH3CN respectively

Sources & evidence

ORD record
ord-5429da1a8918421fb5b6abde8865d958
Source dataset
uspto-grants-2014_12
Patent number
US08921376B2

Reaction notes

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