2-Methylpyridine-4-boronic acid → ethyl 3(2-methylpyridin-4-yl)-1-trityl-4H-indazole-5-carboxylate

HRID 530837Notes

Reaction equation

HRID 530837 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.[CH3:35][C:36]1[CH:41]=[C:40](B(O)O)[CH:39]=[CH:38][N:37]=1>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>[CH3:35][C:36]1[CH:41]=[C:40]([C:2]2[NH: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)[C:5]3[C:10]=2[CH2:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=3)[CH:39]=[CH:38][N:37]=1

Participants

4

Reactant 2

HCID 41926642-Methylpyridine-4-boronic acidHCID 67984870HCID 67984870, compound

Product 1

HCID 86698237ethyl 3(2-methylpyridin-4-yl)-1-trityl-4H-indazole-5-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

ethyl 3-bromo-1-trityl-1H-indazole-5-carboxylate (510 mg, 1.0 mol) was added to a vial containing 2-methylpyridin-4-ylboronic acid (128 mg, 1.04 mol) and tetrakis(triphenylphosphine)palladium (140 mg, 0.104 mol). After purging the vial with nitrogen gas, dioxane (5 mL) and 2M sodium carbonate (5 mL) was added to the vial respectively. The reaction mixture was stirred and was heated to 80° C. for overnight. Upon completion, the mixture was concentrated under vacuo. The mixture was extracted using ethyl acetate (3×100 mL). The extracts were combined and dried using anhydrous sodium sulfate. The resulting mixture was purified using flash chromatography to give the desired compound in 85% yield.

Workup

  1. customAfter purging the vial with nitrogen gas, dioxane (5 mL) and 2M sodium carbonate (5 mL)
  2. additionwas added to the vial respectively
  3. concentrationUpon completion, the mixture was concentrated under vacuo
  4. extractionThe mixture was extracted
  5. customdried
  6. customThe resulting mixture was purified

Sources & evidence

ORD record
ord-e9131e6df75647a78c2e7842937a1530
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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