Hydrochloric Acid → HCID 66738459, compound

HRID 1640895Notes

Reaction equation

HRID 1640895 reaction equation
[BH4-].[Na+].[F:3][C:4]1[N:9]=[CH:8][C:7]([O:10][CH2:11][C:12](=[O:14])[CH3:13])=[C:6]([I:15])[CH:5]=1.Cl.O>CO>[F:3][C:4]1[N:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]([OH:14])[CH3:13])=[C:6]([I:15])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 66738338HCID 66738338, compound

Product 1

HCID 66738459HCID 66738459, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add NaBH4 (35 mg, 0.94 mmol) to a solution of 1-(6-fluoro-4-iodo-pyridin-3-yloxy) propan-2-one (240 mg, 0.81 mmol) in methanol (4 mL) slowly. Stir the mixture at RT for 3 h. Add 1 N HCl and water. Extract with methylene chloride. Wash the organic layer with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo to a yellow solid. Purify by column chromatography (hexane to 10% ethyl acetate in hexane) to afford the title compound as a light yellow solid (240 mg, 99%). MS (ES) m/z 298 [M+1]+.

Workup

  1. extractionExtract with methylene chloride
  2. washWash the organic layer with aqueous saturated sodium chloride
  3. dry with materialDry over sodium sulfate
  4. concentrationConcentrate the solution in vacuo to a yellow solid
  5. customPurify by column chromatography (hexane to 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9efd4c7791ec4db2b8e84b9bb12e97de
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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