Sodium Carbonate → HCID 67996212, compound

HRID 1467343Notes

Reaction equation

HRID 1467343 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[CH:30]=2)[NH:25][N:24]=1>O1CCOCC1.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>[N:12]1[CH:11]=[CH:10][C:9]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[CH:30]=3)[NH:25][N:24]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 178497387HCID 178497387, compound

Product 1

HCID 67996212HCID 67996212, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.965 g, 4.70 mmol), PdCl2(dppf)-CH2Cl2 (0.256 g, 0.314 mmol), sodium carbonate (3.14 mL, 6.27 mmol) and methyl 3-bromo-1H-indazole-5-carboxylate (0.8 g, 3.14 mmol) were taken up in 1,4-dioxane (15 mL). The flask was evacuated and back-filled with N2 (×3) before stirring at 100° C. for 24 hours. Room temperature was attained, the reaction mixture was diluted with MeOH, filtered through Celite and concentrated in vacuo. Purification of the residue by MPLC (12-100% EtOAc-hexanes) gave methyl 3-pyridin-4-yl-1H-indazole-5-carboxylate as a yellow solid.

Workup

  1. customThe flask was evacuated
  2. additionback-filled with N2 (×3)
  3. customRoom temperature
  4. additionthe reaction mixture was diluted with MeOH
  5. filtrationfiltered through Celite
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by MPLC (12-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-5191f7b04c404bc78d4956d0b5e31cd4
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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