Trifluoroacetic acid → HCID 44466932, compound

HRID 383469Notes

Reaction equation

HRID 383469 reaction equation
C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC.[CH3:15][C:16]1[C:20]([C:21]2[N:22]([C:35]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=3)[C:23]3[C:28]([C:29]=2[CH:30](O)[C:31]([NH2:33])=[O:32])=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:19]([CH3:42])[O:18][N:17]=1>>[CH3:15][C:16]1[C:20]([C:21]2[N:22]([C:35]3[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=3)[C:23]3[C:28]([C:29]=2[CH2:30][C:31]([NH2:33])=[O:32])=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:19]([CH3:42])[O:18][N:17]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 44466931HCID 44466931, compound

Product 1

HCID 44466932HCID 44466932, compound

Procedure

1 ml TFA and 19 μl Et3SiH were added to 2-(2-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indol-3-yl)-2-hydroxyacetamide at 0° C. and the mixture was stirred for 60 min. The solvent was evaporated without heating followed by short silica gel purification (EtOAc/heptane; 1:9 to 8:2) to provide 2-(2-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indol-3-yl)acetamide (E37). ES/MS m/z: 362.3 (M+H); 1H NMR (methanol-d3, 500 MHz): 8.98 m, 1H), 8.46-8.35 (m, 5H), 8.16 (m, 2H), 4.78 (d, 2H, J=1.9 Hz), 3.54 (s, 3H) and 3.19 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. temperaturewithout heating
  3. customfollowed by short silica gel purification (EtOAc/heptane; 1:9 to 8:2)

Sources & evidence

ORD record
ord-5d83724789e64af591d488c2f17845f9
Source dataset
uspto-grants-2013_02
Patent number
US08367665B2

Reaction notes

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