2-Fluoroethanol → HCID 178523748, compound

HRID 2042827Notes

Reaction equation

HRID 2042827 reaction equation
[F:1][CH2:2][CH2:3][OH:4].CC(C)([O-])C.[K+].Cl[C:12]1[N:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:13]=1[C:14]([NH:16][CH:17]1[CH2:22][CH2:21][CH:20]([C:23]([F:26])([F:25])[F:24])[CH2:19][CH2:18]1)=[O:15]>C1COCC1.O>[Cl:31][C:29]1[CH:28]=[CH:27][C:13]([C:14]([NH:16][C@H:17]2[CH2:18][CH2:19][C@H:20]([C:23]([F:24])([F:25])[F:26])[CH2:21][CH2:22]2)=[O:15])=[C:12]([O:4][CH2:3][CH2:2][F:1])[N:30]=1

Participants

6

Reactant 3

HCID 97372-FluoroethanolHCID 23665647Potassium tert-butoxideHCID 86669299HCID 86669299, compound

Product 1

HCID 178523748HCID 178523748, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Fluoroethanol (380 μL, 6.45 mmol) is added to potassium tert-butoxide (730 mg, 6.16 mmol) in THF (60 mL) and stirred for 5 min at rt. After the addition of 2,6-dichloro-N-(4-trifluoromethyl-cyclohexyl)-nicotinamide (2.00 g, 5.86 mmol) the reaction mixture is stirred for 1 h hour at rt, then diluted with water and concentrated. The residue is stirred in ice water, the precipitate is filtered off and dried.

Workup

  1. stirringis stirred for 1 h hour at rt
  2. concentrationconcentrated
  3. stirringThe residue is stirred in ice water
  4. filtrationthe precipitate is filtered off
  5. customdried

Sources & evidence

ORD record
ord-dc7ec1cc6de448e2b416d666e5bd0b3e
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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