Sodium Carbonate → HCID 67319636, compound

HRID 244740Notes

Reaction equation

HRID 244740 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.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.[CH3:32][C:33]([C:36]1[NH:47][C:39]2=[N:40][CH:41]=[CH:42][C:43](B(O)O)=[C:38]2[CH:37]=1)([CH3:35])[CH3:34]>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].C(Cl)Cl.CO.O>[CH3:35][C:33]([C:36]1[NH:47][C:39]2=[N:40][CH:41]=[CH:42][C:43]([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:38]2[CH:37]=1)([CH3:32])[CH3:34]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 57416476(2-tert-Butyl-1H-pyrrolo[2,3-b]pyridin-4-yl)boronic acidHCID 58255750N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide

Product 1

HCID 67319636HCID 67319636, compound

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (50 mg), Pd(dppf)Cl2-DCM adduct (12 mg), 2 M sodium carbonate (aq) (0.22 ml), 1,4-dioxane (0.5 ml) and water (0.278 ml) were added to [2-(1,1-dimethylethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]boronic acid (39 mg). The reaction was heated under microwave irradiation at 150° C. for a total of 25 min. The reaction was passed through a silica cartridge, preconditioned with MeOH, washing with MeOH. The solvent was evaporated and the residue purified using the following system:

Workup

  1. washwashing with MeOH
  2. customThe solvent was evaporated
  3. customthe residue purified

Sources & evidence

ORD record
ord-cb68a2b3ab93472eb05b3e4b7e53a65a
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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