Trifluoroacetic acid → HCID 44140043, compound

HRID 2425855Notes

Reaction equation

HRID 2425855 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]([C:12]1[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=1[F:19])O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[F:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([F:19])[C:12]=1[CH2:10][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 67148875HCID 67148875, compound

Product 1

HCID 44140043HCID 44140043, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

The reaction mixture composed of 5.8 g of (2-amino-3-methoxyphenyl)(2,6-difluorophenyl)methanol, 11 ml of triethylsilane (3 eq.), 10 ml of trifluoroacetic acid (3.9 eq.) in 90 ml of dichloromethane is heated for 6 hours at 40° C. After one night at room temperature, the reaction medium is slowly hydrolyzed in the cold state with 6N sodium hydroxide, the organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is purified by filtration on silica H, eluting with dichloromethane, in order to obtain 3.8 g of the expected product.

Workup

  1. waitAfter one night at room temperature
  2. dry with materialthe organic phase is dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. filtrationThe residue is purified by filtration on silica H
  5. washeluting with dichloromethane, in order

Sources & evidence

ORD record
ord-f813436110ea41df905f9053e0eb23f3
Source dataset
uspto-grants-2011_06
Patent number
US07968534B2

Reaction notes

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