Trifluoroacetic acid → HCID 59814830, compound

HRID 2116634Notes

Reaction equation

HRID 2116634 reaction equation
[CH2:1]([C:3]([C:7]1[S:11][C:10]([S:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)=[CH:18][C:19](=[O:23])[O:20]3)=[CH:15][CH:14]=2)=[N:9][CH:8]=1)(O)[CH2:4][CH3:5])[CH3:2].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([CH:3]([C:7]1[S:11][C:10]([S:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)=[CH:18][C:19](=[O:23])[O:20]3)=[CH:15][CH:14]=2)=[N:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052Triethylsilane2×HCID 59814844HCID 59814844, compound

Product 1

HCID 59814830HCID 59814830, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 7-{[5-(1-ethyl-1-hydroxypropyl)-1,3-thiazol-2-yl]thio}-4-(4-fluorophenyl)-2H-chromen-2-one (26 mg, 0.06 mmol) in 1 mL of CH2Cl2 at 0° C. was added triethylsilane (100 μL) and TFA (100 μL). The mixture was stirred for 1 h at 0° C. then warmed to room temperature with more triethylsilane (250 μL). The solvent was removed in vacuo and chromatographed on silica gel (hexane:EtOAc; 90:10 to 80:20) to yield the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. customchromatographed on silica gel (hexane:EtOAc; 90:10 to 80:20)

Sources & evidence

ORD record
ord-32771a98f43c4750ac39338b1b336c0a
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Reaction notes

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