2,2,2-Trifluoroethanol → HCID 118036602, compound

HRID 1777947Notes

Reaction equation

HRID 1777947 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[F:11][C:12]([F:16])([F:15])[CH2:13][OH:14].[NH2:17][C:18]1[CH:25]=[C:24](F)[C:21]([C:22]#[N:23])=[CH:20][N:19]=1>C1COCC1>[NH2:17][C:18]1[CH:25]=[C:24]([O:14][CH2:13][C:12]([F:16])([F:15])[F:11])[C:21]([C:22]#[N:23])=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 1180369016-Amino-4-fluoronicotinonitrile2×

Product 1

HCID 118036602HCID 118036602, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of KHMDS in THF (1 M, 16.1 ml, 16.04 mmol) was added drop wise to a solution of 2,2,2-trifluoroethanol (0.53 ml, 7.29 mmol) in THF (40 ml) at room temperature. After 2 min a solution of 6-amino-4-fluoronicotinonitrile (intermediate 21, 1.0 g, 7.29 mmol) in THF (10 ml) was added and the reaction mixture stirred for 2 h at room temperature. The reaction mixture was partitioned between saturated aqueous NH4Cl and EtOAc, extracted with EtOAc (2×), the combined organic layers were dried over Na2SO4 and evaporated. The residue was triturated with Et2O and heptane to give the title compound. (UPLC-MS 7) tR 0.70; ESI-MS 218.1 [M+H]+.

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous NH4Cl and EtOAc
  2. extractionextracted with EtOAc (2×)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. customevaporated
  5. customThe residue was triturated with Et2O and heptane

Sources & evidence

ORD record
ord-bd5f8927e2534e0580dcca61bb0223e1
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

Loading…