Sodium Carbonate → Ethyl 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylate

HRID 1467302Notes

Reaction equation

HRID 1467302 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[N:4]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[N:35]1[CH:40]=[CH:39][C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O1CCOCC1>[N:35]1[CH:40]=[CH:39][C:38]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=3)[N:4]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:3]=2)=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 67984870HCID 67984870, compound

Product 1

HCID 67996877Ethyl 3-pyridin-4-yl-1-trityl-1H-indazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 5 ml microwave vial equipped with a stir bar was added ethyl 3-bromo-1-trityl-1H-indazole-5-carboxylate (1095.3 mg, 2.142 mmol), pyridine-4-boronic acid pinacol ester (679 mg, 3.21 mmol), sodium carbonate (2142 μl, 4.28 mmol), dioxane (1.07E+04 μl), and PalladiumTetrakis (247 mg, 0.214 mmol). The vial was purged with nitrogen, and was then sealed and heated to 80° C. for 24 h. LCMS taken after 24 hours indicates formation of the desired product. The crude reaction mixture was filtered through a column pre-packed with celite. The combined organics were concentrated under reduced pressure and the material was dry loaded onto a 100 g column. A column was run from 100% hexanes to 100% ethyl acetate. The desired product eluted; fractions were collected and concentrated in vacuo

Workup

  1. customTo a 5 ml microwave vial equipped with a stir bar
  2. customThe vial was purged with nitrogen
  3. customwas then sealed
  4. customThe crude reaction mixture
  5. filtrationwas filtered through a column pre-packed with celite
  6. concentrationThe combined organics were concentrated under reduced pressure
  7. customthe material was dry
  8. washThe desired product eluted
  9. customfractions were collected
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2198061c104b4a368590e5be3d3add7e
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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