Sodium Hydroxide → HCID 178481726, compound

HRID 520525Notes

Reaction equation

HRID 520525 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]#[N:13])[C:5]2[CH:6]=[N:7][N:8]([CH3:11])[C:9]=2[CH:10]=1.C([Sn](CCCC)=O)CCC.C[Si]([N:28]=[N+:29]=[N-:30])(C)C.[OH-].[Na+]>C1(C)C=CC=CC=1.CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([C:12]2[NH:30][N:29]=[N:28][N:13]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 61221Dibutyltin oxideHCID 78378Azidotrimethylsilane2×HCID 666923166-Bromo-1-methyl-1H-indazole-4-carbonitrile

Product 1

HCID 178481726HCID 178481726, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

6-Bromo-1-methyl-1H-indazole-4-carbonitrile (514 mg, 2.177 mmol) was dissolved in toluene (20 mL) and dibutyl(oxo)stannane (108 mg, 0.435 mmol) and trimethylsilyl azide (0.573 mL, 4.35 mmol) were added over 2 mins. The mixture was then stirred at 110° C. under nitrogen for 28 h. Further trimethylsilyl azide (0.03 mL, 0.228 mmol) was added and the mixture continued stirring at 110° C. under nitrogen for 44 h. The solvent was removed in vacuo to give a white solid. 2M sodium hydroxide in methanol was added and the mixture heated to 50° C. and then filtered whilst hot to remove insoluble impurities. The filtrate was cooled and then acidified via dropwise addition of 2M hydrochloric acid. The resultant precipitate was filtered and dried in a vacuum oven to give the title compound as a white solid (604 mg).

Workup

  1. stirringthe mixture continued stirring at 110° C. under nitrogen for 44 h
  2. customThe solvent was removed in vacuo
  3. customto give a white solid
  4. temperaturethe mixture heated to 50° C.
  5. filtrationfiltered whilst hot
  6. customto remove insoluble impurities
  7. temperatureThe filtrate was cooled
  8. additionacidified via dropwise addition of 2M hydrochloric acid
  9. filtrationThe resultant precipitate was filtered
  10. customdried in a vacuum oven

Sources & evidence

ORD record
ord-b3fa9fc646e34c86b7664385148ee5d7
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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