Sodium 2-propanethiolate → HCID 118036810, compound

HRID 1778034Notes

Reaction equation

HRID 1778034 reaction equation
[CH3:1][CH:2]([S-:4])[CH3:3].[Na+].[NH2:6][C:7]1[CH:14]=[C:13](F)[C:10]([C:11]#[N:12])=[CH:9][N:8]=1>C1COCC1>[NH2:6][C:7]1[CH:14]=[C:13]([S:4][CH:2]([CH3:3])[CH3:1])[C:10]([C:11]#[N:12])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 3470666Sodium 2-propanethiolate2×HCID 1180369016-Amino-4-fluoronicotinonitrile2×

Product 1

HCID 118036810HCID 118036810, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium propane-2-thiolate (1.59 g, 15.68 mmol) was added to 6-amino-4-fluoronicotinonitrile (intermediate 21, 2.15 g, 15.68 mmol), in THF (75 ml) and the mixture stirred for 16 h at room temperature. Additional sodium propane-2-thiolate (1.59 g, 15.68 mmol) was added and the reaction stirred at room temperature for a further 4 days, then partitioned between saturated aqueous NaHCO3 solution and EtOAc, the combined organic layers washed with brine, dried over MgSO4 and evaporated. The residue was purified by normal phase chromatography: 80 g RediSep® column, eluting with a gradient from heptane to EtOAc. Product containing fractions were combined, evaporated and recrystallised from EtOAc to give the title compound as a white solid. (UPLC-MS 3) tR 0.78; ESI-MS 194.0 [M+H]+.

Workup

  1. stirringthe reaction stirred at room temperature for a further 4 days
  2. custompartitioned between saturated aqueous NaHCO3 solution and EtOAc
  3. washthe combined organic layers washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by normal phase chromatography
  7. wash80 g RediSep® column, eluting with a gradient from heptane to EtOAc
  8. additionProduct containing fractions
  9. customevaporated
  10. customrecrystallised from EtOAc

Sources & evidence

ORD record
ord-1bbd70d4db8e4f628b5d840a7e7497ac
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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