Isopropylethanediol → HCID 86661732, compound

HRID 1020825Notes

Reaction equation

HRID 1020825 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH:16]([O:19][CH2:20][CH2:21][OH:22])([CH3:18])[CH3:17].[H-].[Na+]>CN(C=O)C>[Cl:11][C:9]1[C:8]([C:12]([F:15])([F:14])[F:13])=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([O:22][CH2:21][CH2:20][O:19][CH:16]([CH3:18])[CH3:17])[N:10]=1

Participants

5

Reactant 3

HCID 7996IsopropylethanediolHCID 24758Sodium hydrideHCID 86661733HCID 86661733, compound

Product 1

HCID 86661732HCID 86661732, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-dichloro-5-(trifluoromethyl)nicotinamide (0.35 g, 1.35 mmol) and 2-isopropoxyethanol (0.14 g, 1.35 mol) in DMF (20 mL) was added sodium hydride (59 mg, 1.48 mmol) in portions at 0° C. The mixture was stirred at r.t for 2 hrs, quenched by water, extracted by EtOAc and the organic layer was concentrated in vacuo to afford 6-chloro-2-(2-isopropoxyethoxy)-5-(trifluoromethyl)nicotinamide (0.2 g, 45.4%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 8.45 (s, 1H), 8.05 (bs, 1H), 7.63 (bs, 1H), 4.54-4.52 (m, 2H), 3.75-3.72 (m, 2H), 3.64-3.58 (m, 1H), 1.07-1.06 (d, 6H).

Workup

  1. customquenched by water
  2. extractionextracted by EtOAc
  3. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-fe884508994345e888ebf9b4fa7dcafa
Source dataset
uspto-grants-2014_05
Patent number
US08716478B2

Reaction notes

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