Pyridine → HCID 86669035, compound

HRID 2370990Notes

Reaction equation

HRID 2370990 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:8]([CH:23]=O)[C:9]3[C:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:25])[O:4][N:3]=1.Cl.[NH2:27][OH:28].N1C=CC=CC=1.CCOC(C)=O>CO>[CH3:1][C:2]1[C:6]([C:7]2[N:8]([CH:23]=[N:27][OH:28])[C:9]3[C:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:25])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 67108937HCID 67108937, compound

Product 1

HCID 86669035HCID 86669035, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbaldehyde (18 mg, 0.05 mmol) was dissolved in 5 ml MeOH. 5 eq hydroxylamine hydrochloride and 6 eq pyridine were added. The mixture was heated at reflux for 1.5 h and then allowed to cool to rt. 50 ml EtOAc were added, the resulting mixture was washed with brine 3× and then dried over Na2SO4. The solvent was concentrated and the crude product was purified using preparative HPLC. 3.5 mg 2-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbaldehyde oxime was obtained. The title compound was identified by 1H-NMR which showed that the oxime product was a single isomer, but did not confirm whether the (E) or (Z) oxime isomer had been obtained. ES/MS m/z: 348.01 (M+H), 346.18 (M−H); 1H NMR (MeOD, 500 MHz): 8.38 (s, 1H), 8.26 (m, 1H), 7.66 (m, 1H), 7.35 (m, 1H), 7.25 (m, 1H), 7.11 (m, 2H), 6.80 (m, 2H), 2.13 (s, 3H) and 1.99 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. washthe resulting mixture was washed with brine 3×
  4. dry with materialdried over Na2SO4
  5. concentrationThe solvent was concentrated
  6. customthe crude product was purified

Sources & evidence

ORD record
ord-65822f457c41493aab04a832729e296d
Source dataset
uspto-grants-2014_04
Patent number
US08710243B2

Reaction notes

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