Sodium Hydroxide → HCID 66598539, compound

HRID 1189174Notes

Reaction equation

HRID 1189174 reaction equation
Br[CH2:2][CH2:3][C:4]#[C:5][Si:6]([CH3:9])([CH3:8])[CH3:7].[F:10][C:11]1[CH:19]=[CH:18][C:14]2[NH:15][N:16]=[N:17][C:13]=2[CH:12]=1.[OH-].[Na+]>>[F:10][C:11]1[CH:19]=[CH:18][C:14]2=[N:15][N:16]([CH2:2][CH2:3][C:4]#[C:5][Si:6]([CH3:9])([CH3:8])[CH3:7])[N:17]=[C:13]2[CH:12]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 642593silane, (4-bromo-1-butynyl)trimethyl-HCID 178505476HCID 178505476, compound

Product 1

HCID 66598539HCID 66598539, compoundYield 100%

Conditions

Temperature
100 °C

Procedure

(4-Bromo-but-1-ynyl)-trimethyl-silane (294 mg, 1.43 mmol) was added to a solution of 5-fluoro-1H-benzo[d][1,2,3]triazole (187 mg, 1.36 mmol) in a solution of NaOH (2N, 955 μL). The reaction mixture was heated at 100° C. for 14 hours, then it was cooled down and was extracted with DCM. The organic phase was washed with water, brine, dried over MgSO4, filtered and evaporated to yield 355 mg (1.36 mmol) 5-fluoro-2-(4-trimethylsilanyl-but-3-ynyl)-2H-benzo[d][1,2,3]triazole including the two others isomers.

Workup

  1. temperatureit was cooled down
  2. extractionwas extracted with DCM
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-3b1664549c054ec3a497dc7a2caf7441
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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