Trifluoroacetic acid → HCID 57908163, compound

HRID 513088Notes

Reaction equation

HRID 513088 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([I:9])[CH:3]=1.[Si]([O:17][CH2:18][CH:19]=O)(C(C)(C)C)(C)C.FC(F)(F)C(O)=O.[BH3-]C#N.[Na+]>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH2:19][CH2:18][OH:17])=[C:4]([I:9])[CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 184070406-Chloro-4-iodopyridin-3-amine

Product 1

HCID 57908163HCID 57908163, compoundYield 190.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-chloro-4-iodopyridin-3-amine (6.5 g, 25.5 mmol) in CH3OH (1500 mL) was added 2-(tert-butyldimethylsilyloxy)acetaldehyde (18.0 g, 103 mmol). Then trifluoroacetic acid (150 mL) and NaBH3CN (8.0 g, 127 mmol) were added slowly at 0° C. The mixture was allowed to warm to 25° C. and the stirring was continued for an additional 12 hours. The mixture was concentrated under reduced pressure and treated with NaOH (3M) to pH=8. The aqueous layer was extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4. The solvent was concentrated in vacuo to afford crude product 2-(6-Chloro-4-iodopyridin-3-ylamino)ethanol (14.5 g), that was used in the next step without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiontreated with NaOH (3M) to pH=8
  3. extractionThe aqueous layer was extracted with ethyl acetate (100 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-9fd3a1268fa64390b9d5dceb82aae653
Source dataset
uspto-grants-2015_08
Patent number
US09102672B2

Reaction notes

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