1,1,1-Trifluoro-2-propanol → HCID 68850676, compound

HRID 1820978Notes

Reaction equation

HRID 1820978 reaction equation
Cl[C:2]1[C:12]([I:13])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[F:14][C:15]([F:20])([F:19])[CH:16]([OH:18])[CH3:17].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[I:13][C:12]1[C:2]([O:18][CH:16]([CH3:17])[C:15]([F:20])([F:19])[F:14])=[N:3][CH:4]=[C:5]([CH:11]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 97741,1,1-Trifluoro-2-propanolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86057428HCID 86057428, compound

Product 1

HCID 68850676HCID 68850676, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 120 mg (0.39 mmol) of ethyl 6-chloro-5-iodonicotinate (from Step A) and 52 μL (0.58 mmol) of 1,1,1-trifluoro-2-propanol in 5 mL of THF at rt was added 578 μL (0.58 mmol) of sodium bis(trimethylsilyl)amide (1.0 M in THF). After refluxing overnight, the reaction mixture was concentrated. Chromatography on a Biotage 40S cartridge using 1:49 v/v Et2O/hexanes as the eluant gave 73 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.39 (t, J=7.1, 3H), 1.55 (d, J=6.6, 3H), 4.38 (q, J=7.1, 2H), 5.79 (m, 1H), 8.66 (d, J=2.1, 1H), 8.73 (d, J=2.0, 1H).

Workup

  1. temperatureAfter refluxing overnight
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d86f28bfa2874ae0b0a4594f30648e7d
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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