Lithium hydride → HCID 19390724, compound

HRID 1756592Notes

Reaction equation

HRID 1756592 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[N:7]3[C:18]4[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=4)[C:12](=[O:20])[C:8]3=[N:9]2)=[CH:4][CH:3]=1.[C:22](=[O:29])([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[NH2:23].[H-].[Li+]>CN(C=O)C.C(Cl)(Cl)Cl>[C:25]([O:24][C:22]([NH:23][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[N:7]3[C:18]4[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=4)[C:12](=[O:20])[C:8]3=[N:9]2)=[CH:4][CH:3]=1)=[O:29])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 62714Lithium hydrideHCID 77922tert-Butyl carbamateHCID 4786513,8-Difluoro-indolo(2,1-b)quinazoline-6,12-dione

Product 1

HCID 19390724HCID 19390724, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3,8-difluoroindolo[2,1-b]quinazoline-6,12-dione (0.1 mmol, Example 36), t-butyl carbamate (0.11 mmol) and lithium hydride (0.12 mmol) in DMF (0.1 mM) is stirred at 70° C. for 12 h. The resulting reaction mixture is diluted with chloroform, washed with 0.1N HCl, sodium bicarbonate solution, dried (MgSO4) and the solvent is evaporated. Silica gel chromatography (1% MeOH/CHCl3) gives 3-(N-t-butyloxycarbonylamino)-8-fluoroindolo[2,1-b]quinazoline-6,12-dione.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with 0.1N HCl, sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-f151057b30fb41e193b6cad9889bf0ee
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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