Ethyl Acetate → HCID 86615783, compound

HRID 1926132Notes

Reaction equation

HRID 1926132 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:23]([N:24](C)[C:25](=O)C(F)(F)F)=[C:22]([I:32])[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[CH:10]=1.[BH4-].[Na+].C(OCC)(=O)C>C(O)(C)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:23]([NH:24][CH3:25])=[C:22]([I:32])[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:15]#[N:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 86615782HCID 86615782, compound

Product 1

HCID 86615783HCID 86615783, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

To a solution of N-(4-{[3-chloro-4-(3-cyanophenoxy)phenyl]amino}-6-iodopyrimidin-5-yl)-2,2,2-trifluoro-N-methylacetamide (1.0 g) in isopropanol-tetrahydrofuran (5.0 mL-10 mL) was added sodium borohydride (70 mg) at room temperature. The mixture was stirred at room temperature for 1.5 hrs, and ethyl acetate was added. The mixture was washed with water and saturated brine and the organic layer was dried over magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=4:1→3:2) to give the title compound (755 mg) as a white amorphous solid.

Workup

  1. washThe mixture was washed with water and saturated brine
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was separated
  5. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=4:1→3:2)

Sources & evidence

ORD record
ord-9c68a4ea3a7c4fe99a812eda674d3ab4
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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