Ammonium Chloride → 4-(4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-ol

HRID 1846203Notes

Reaction equation

HRID 1846203 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=N[CH:7]=1.[CH:12]([Mg]Br)(C)C.[O:17]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[CH2:19][CH2:18]1.[NH4+].[Cl-]>C1COCC1>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:4]=[CH:3][C:2]([C:20]2([OH:27])[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:26]3[O:17][CH2:18][CH2:19]2)=[CH:7][CH:12]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 27611975-Bromo-2-(trifluoromethyl)pyridineHCID 450796202,3-Dihydro-4H-pyrano[3,2-b]pyridin-4-oneHCID 178418365HCID 178418365, compound

Product 1

HCID 899648884-(4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of 5-bromo-2-(trifluoromethyl)pyridine (0.604 g, 2.68 mmol) in THF (10 mL) was added isopropyl magnesium bromide (1 mL, 2.68 mmol) in a drop-wise fashion. The reaction mixture was stirred in a cooling bath for 1 h and was then treated with 2H-pyrano[3,2-b]pyridin-4(3H)-one (200 mg, 1.34 mmol) in THF (5 mL). After stirring for 1 h, saturated NH4Cl (50 mL) was added to the reaction mixture, and the aqueous solution was extracted with EtOAc (3×10 mL). The combined organic layers were dried over Na2SO4, and concentrated. The residue was purified by column chromatography to give the desired alcohol.

Workup

  1. stirringAfter stirring for 1 h
  2. extractionthe aqueous solution was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d06ce9253b2041e3b5b3deadddce1426
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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