Sodium Carbonate → HCID 44539959, compound

HRID 244728Notes

Reaction equation

HRID 244728 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([NH:11][C:12]([C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)=[O:13])[CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[C:29]=2[NH2:35])O1.[C:37](=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH:35]1[C:29]2[CH:28]=[CH:33][CH:32]=[C:31]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][NH:8]4)=[C:4]([NH:11][C:12]([C:14]4[N:15]=[C:16]([CH3:19])[S:17][CH:18]=4)=[O:13])[CH:3]=3)[C:30]=2[N:34]=[CH:37]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 58255750N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamideHCID 666177883-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzenediamine

Product 1

HCID 44539959HCID 44539959, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (200 mg), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzenediamine (167 mg) (WO2006/005915, page 90-91), Pd(dppf)Cl2 (43 mg) and 2M sodium carbonate (0.890 ml) were charged in 1,4-dioxane (2 ml) and water (2 ml). The reaction vial was sealed and heated under microwave irradiation at 150° C. for 15 min. The reaction was extracted with DCM (3×30 ml). The combined organic layers were evaporated. To a solution of the residue in DMF (3 ml) was added triethylorthoformate (10 ml) and the mixture heated at reflux for 2 h. The solvent was evaporated and the residue dissolved in methanol:DMSO (3 ml, 1:1) and purified by mass directed preparative HPLC (Method A) to give title compound (26 mg).

Workup

  1. customThe reaction
  2. customvial was sealed
  3. extractionThe reaction was extracted with DCM (3×30 ml)
  4. customThe combined organic layers were evaporated
  5. additionTo a solution of the residue in DMF (3 ml) was added triethylorthoformate (10 ml)
  6. temperaturethe mixture heated
  7. temperatureat reflux for 2 h
  8. customThe solvent was evaporated
  9. dissolutionthe residue dissolved in methanol
  10. customDMSO (3 ml, 1:1) and purified by mass

Sources & evidence

ORD record
ord-95aa02e24175454aaeb1d146d5cf8e64
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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