Hydrochloric Acid → HCID 87198318, compound

HRID 1690217Notes

Reaction equation

HRID 1690217 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([C:12]1[CH:28]=[CH:27][C:15]([O:16][C:17]2[CH:18]=[C:19]([C:23]([I:26])=[CH:24][N:25]=2)[C:20](O)=[O:21])=[C:14]([CH2:29][CH2:30][CH3:31])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].B.O1CCCC1.[OH-].[Na+].Cl>O1CCCC1.O>[F:33][C:2]([F:1])([F:32])[C:3]([C:12]1[CH:28]=[CH:27][C:15]([O:16][C:17]2[CH:18]=[C:19]([CH2:20][OH:21])[C:23]([I:26])=[CH:24][N:25]=2)=[C:14]([CH2:29][CH2:30][CH3:31])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 86639432HCID 86639432, compound

Product 1

HCID 87198318HCID 87198318, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propy phenoxy)-5-iodoisonicotinic acid (441 mg, 0.741 mmol) in tetrahydrofuran (3.7 mL), a solution of borane-tetrahydrofuran (2.97 mL, 1 M in THF solution) was added under ice-cold conditions, and the resultant mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, water, 1N aqueous solution of sodium hydroxide and 5% aqueous solution of hydrochloric acid were added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and dried using sodium sulfate. The organic layer was concentrated in vacuo, and the obtained residue was purified using column chromatography (hexane/ethyl acetate). (2-(4-(1,1,1,3,3,3-Hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propylphenoxy)-5-iodopyridin-4-yl)methanol (391 mg, yield 91%) was obtained as a yellow oil.

Workup

  1. additionwere added to the reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. customdried
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe obtained residue was purified

Sources & evidence

ORD record
ord-faa38464745541548a581f8a7a503aac
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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