3-Aminophenol → HCID 71060547, compound

HRID 1038445Notes

Reaction equation

HRID 1038445 reaction equation
Cl[C:2]1[O:3][C:4]([C:7]2[N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([F:16])=[CH:11][CH:10]=3)=[CH:5][N:6]=1.[NH2:24][C:25]1[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=1>CC(O)C>[F:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:7]([C:4]1[O:3][C:2]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=3)=[N:6][CH:5]=1)=[CH:15]2

Participants

4

Reactant 2

HCID 115683-AminophenolHCID 71060343HCID 71060343, compound

Product 1

HCID 71060547HCID 71060547, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butyl 2-(2-chlorooxazol-5-yl)-5-fluoro-1H-indole-1-carboxylate 50 (0.308 g, 0.916 mmol) and commercially available 3-aminophenol 8 (0.10 g, 0.916 mmol) in 2-propanol (20 mL) was heated to 80° C. for 18 h with stirring. Upon cooling, solvent was evaporated and silica column purified (Biotage) (Acetone/hexane as an eluent) to provide tert-butyl 5-fluoro-2-(2-((3-hydroxyphenyl)amino)oxazol-5-yl)-1H-indole-1-carboxylate 51 (0.15 g, 40% yield) as solid. MS (ES) m/z 410 (M+H+).

Workup

  1. temperatureUpon cooling
  2. customsolvent was evaporated
  3. customsilica column purified (Biotage) (Acetone/hexane as an eluent)

Sources & evidence

ORD record
ord-957c94e29d4443939e346d9e7ea7d5c3
Source dataset
uspto-grants-2013_10
Patent number
US08551992B2

Reaction notes

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