Methanol → HCID 86597106, compound

HRID 1297276Notes

Reaction equation

HRID 1297276 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]=O)=[C:16]2[CH3:26])=[CH:11][C:10]=1[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:29][OH:30].CO>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]=[N:29][OH:30])=[C:16]2[CH3:26])=[CH:11][C:10]=1[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 86597103HCID 86597103, compound

Product 1

HCID 86597106HCID 86597106, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 1-(4-benzyloxy-3-fluorophenyl)-2-methyl-1H-indole-3-carbaldehyde (0.81 g, 2.3 mmol), hydroxylamine hydrochloride (0.25 g, 3.6 mmol) and methanol (25 mL) was added pyridine (1 mL). The reaction mixture was heated to reflux and held for 30 min. The mixture was cooled, the methanol removed by evaporation and the residue taken up in ethyl acetate/water. The product was extracted into ethyl acetate (2×50 mL), the ethyl acetate washed with water and brine and dried over MgSO4. The solvent was evaporated, and the crude product was purified by silica gel chromatography (25% ethyl acetate-hexanes) to provide a white solid (0.7 gr, 83%): mp 167-168° C.; 1H NMR (DMSO-d6): δ 2.32 (3H, s), 5.29 (2H, s), 6.99-7.01 (1H, m), 7.10-7.17 (2H, m), 7.25-7.28 (1H, m), 7.37-7.42 (1H, m), 7.43-7.49 (3H, m), 7.49-7.54 (2H, m), 8.01-8.04 (1H, m), 8.41 (1H, s), 10.67 (1H, s); MS m/z (M+H)+ 375: Anal. for C23H19FN2O2: Calc'd: C, 73.78; H, 5.11; N, 7.48. Found: C, 73.53; H, 5.06; N, 7.32

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was cooled
  4. customthe methanol removed by evaporation
  5. extractionThe product was extracted into ethyl acetate (2×50 mL)
  6. washthe ethyl acetate washed with water and brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated
  9. customthe crude product was purified by silica gel chromatography (25% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-d258dca0e7d543b196023bf8b96f06df
Source dataset
uspto-grants-2007_07
Patent number
US07250440B2

Reaction notes

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