Trifluoroacetic acid → 3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenol

HRID 1035808Notes

Reaction equation

HRID 1035808 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[O:10][C:11]([C:14]3[N:15](C(OC(C)(C)C)=O)[C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:12][N:13]=2)[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[C:14]1[C:11]1[O:10][C:9]([NH:8][C:4]2[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=2)=[N:13][CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060496tert-butyl 2-(2-((3-hydroxyphenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate

Product 1

HCID 710604143-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenolYield 29.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl 2-(2-((3-hydroxyphenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate 22 (0.125 g, 0.319 mmol) in anhydrous CH2Cl2 (20 mL) was added 1:1 mixture of CH2Cl2:Trifluoroacetic acid (5 mL) at 0° C. Reaction was stirred for 1 hour at ambient temperature. It was quenched with aq. saturated NaHCO3 and CH2Cl2 layer was separated. After evaporation of solvent, crude product was purified using preparative-TLC to obtain 3-((5-(1H-indol-2-yl)oxazol-2-yl)amino)phenol 23 (0.027 g, 16% yield).

Workup

  1. customat 0° C
  2. customReaction
  3. customIt was quenched with aq. saturated NaHCO3 and CH2Cl2 layer
  4. customwas separated
  5. customAfter evaporation of solvent, crude product
  6. customwas purified

Sources & evidence

ORD record
ord-29391ef0a25e42698348c9a534c22e59
Source dataset
uspto-grants-2013_10
Patent number
US08546400B2

Reaction notes

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