Water → 2-(Propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl thiocyanate

HRID 2118790Notes

Reaction equation

HRID 2118790 reaction equation
[CH:1]([C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[S-:13][C:14]#[N:15].[K+].BrBr.O>CO.[Br-].[K+]>[CH:1]([C:4]1[C:12]([S:13][C:14]#[N:15])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24408BromineHCID 516872Potassium thiocyanateHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Product 1

HCID 137714612-(Propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl thiocyanateYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 253877Potassium BromideSolvent

Procedure

To a solution of 3 g of 2-isopropylpyrazolo[1,5-a]pyridine in 56 ml of methanol was added 5.74 g of potassium thiocyanate and stirred at room temperature. 3.3 g of bromine was dissolved in 13 ml of methanol saturated with potassium bromide and added dropwise to the previous solution. Then, the mixture was stirred at room temperature for an hour, poured into 130 ml of water and resulting precipitate was filtered and dried. This crude precipitate was recrystallized from methanol to give 3.53 g (yield 87%) of the aimed compound as pale yellow prismatic crystals. mp 91°-92.5° C.

Workup

  1. additionadded dropwise to the previous solution
  2. stirringThen, the mixture was stirred at room temperature for an hour
  3. customresulting precipitate
  4. filtrationwas filtered
  5. customdried
  6. customThis crude precipitate was recrystallized from methanol

Sources & evidence

ORD record
ord-2ffbdf1995e74a1598b35f27ce5f58fb
Source dataset
uspto-grants-1987_07
Patent number
US04680398

Reaction notes

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