Sodium Carbonate → HCID 44540226, compound

HRID 1616049Notes

Reaction equation

HRID 1616049 reaction equation
Br[C:2]1[C:3]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:29](B(O)O)([CH3:31])=[CH2:30].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:24]1[C:25]2[C:21](=[C:20]([C:18]3[CH:17]=[C:16]4[C:12]([CH:13]=[N:14][NH:15]4)=[C:11]([NH:10][C:8]([C:3]4[C:2]([C:29]([CH3:31])=[CH2:30])=[CH:7][CH:6]=[CH:5][N:4]=4)=[O:9])[CH:19]=3)[CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 44540591HCID 44540591, compound

Product 1

HCID 44540226HCID 44540226, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

3-Bromo-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (0.25 g, 0.58 mmol) and isopropenylboronic acid pincaol ester (available from Aldrich, 0.12 ml, 0.64 mmol) were placed in a microwave vial and dissolved in 1,4-dioxane (4 ml). Pd(PPh3)4 (66 mg, 0.06 mmol) and Na2CO3 (0.58 ml, 1.16 mmol, 2 M aqueous solution) were added and the mixture was heated at 150° C. for 10 mins under microwave irradiation. The reaction mixture was filtered through Celite, washing with ethyl acetate. The organic mixture was washed with water (10 ml) and brine (10 ml), dried over MgSO4, filtered and the solvent was removed in vacuo. The resulting orange solid was purified by mass-directed automated preparative HPLC (Method B) to give the title compound as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashing with ethyl acetate
  3. washThe organic mixture was washed with water (10 ml) and brine (10 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe resulting orange solid was purified

Sources & evidence

ORD record
ord-832dc71ef65d490f96b56fb9b2443161
Source dataset
uspto-grants-2014_07
Patent number
US08765743B2

Reaction notes

Loading…