Water → HCID 10017985, compound

HRID 1683923Notes

Reaction equation

HRID 1683923 reaction equation
[CH3:1][NH:2][C:3](=O)[CH2:4][CH:5]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=O)[CH:16]=2)[NH:11][CH:10]=1)[C:6](N)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].O>O1CCCC1.C(OCC)(=O)C>[CH2:19]([NH:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:6]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 53634054HCID 53634054, compound

Product 1

HCID 10017985HCID 10017985, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-methyl-3-(5-phenylcarbonylaminoindol-3-yl)succinamide (18.31 g, 52.71 mmol) in anhydrous tetrahydrofuran (270 mL) at 0° C. was added lithium aluminum hydride (20.01 g, 527 mmol, 10 eq) as a solid portionwise over 45 minutes. The resulting reaction mixture was stirred at room temperature under nitrogen for 24 hours. Sodium sulfate decahydrate (50 g) was then carefully added to the reaction mixture followed by water (5 mL) and ethyl acetate (100 mL). The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. The residual oil was column chromatographed using silica gel (approximately 500 g) and elution with ethyl acetate: methanol: triethylamine [gradient 9:0:1 to 8:1:1] to afford the title compound (7.90 g, 49%) as a pale yellow oil: 13C NMR (acetone-d6) δ142.9, 142.1, 132.3. 129.3, 128.6, 127.5, 121.9, 118.6, 112.8, 112.5, 102.0, 63.6, 57.1, 49.9, 42.8, 36.5, 33.0; FAB LRMS (m/z, relative intensity) 306 (MH+, 100), 263 (4), 248 (4), 223 (8).

Workup

  1. customThe resulting reaction mixture
  2. stirringThe resulting mixture was stirred at room temperature for 1 hour
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customchromatographed
  6. washsilica gel (approximately 500 g) and elution with ethyl acetate

Sources & evidence

ORD record
ord-1b81bf8a9a1b4d97a016a10888a9bc19
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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