1H-Indazole → HCID 57691801, compound

HRID 1189143Notes

Reaction equation

HRID 1189143 reaction equation
Br[CH2:2][CH2:3][C:4]#[C:5][Si:6]([CH3:9])([CH3:8])[CH3:7].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[N:11]1.C([O-])([O-])=O.[K+].[K+].C[Si](C)(C)C#CCCN1C2C(=CC=CC=2)C=N1>CC(C)=O.O>[CH3:7][Si:6]([CH3:9])([CH3:8])[C:5]#[C:4][CH2:3][CH2:2][N:11]1[CH:12]=[C:13]2[C:18]([CH:17]=[CH:16][CH:15]=[CH:14]2)=[N:10]1

Participants

7

Reactant 4

HCID 92211H-IndazoleHCID 11430Potassium CarbonateHCID 642593silane, (4-bromo-1-butynyl)trimethyl-HCID 66598009HCID 66598009, compound

Product 1

HCID 57691801HCID 57691801, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of (4-bromo-but-1-ynyl)-trimethyl-silane (374 mg, 1.83 mmol), indazole (200 mg, 1.69 mmol) and K2CO3 (459 mg, 3.32 mmol) in acetone (2 mL) was heated at 150° C. for 900 s in a microwave. After the addition of water, acetone was evaporated. The aqueous phase was extracted with DCM. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated to yield 250 mg (1.03 mmol, 62%) of 2-(4-trimethylsilanyl-but-3-ynyl)-2H-indazole and 1-(4-trimethylsilanyl-but-3-ynyl)-1H-indazole.

Workup

  1. customwas evaporated
  2. extractionThe aqueous phase was extracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-088b55f05e2e4eed95a7caa374fa5b2d
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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