Methanol → (2-Ethyl-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

HRID 1064186Notes

Reaction equation

HRID 1064186 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH:17]=[CH2:18])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.CO>[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH2:17][CH3:18])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 6228DimethylformamideHCID 136141708(6-Oxo-2-vinyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

Product 1

HCID 135984714(2-Ethyl-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl esterYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium (10% on activated carbon) (0.23 g, 0.198 mmol) was added to a solution of the title compound of Example 164 (0.65 g, 1.99 mmol) in 1:10 N,N-dimethylformamide: methanol (11 mL). The reaction mixture was purged with H2 and stirred at room temperature under H2 (1 atm.) for 5 hours. The palladium was filtered and the volatile components were removed in vacuo. The resulting residue was dissolved in methanol and loaded onto a silica gel plug. The plug was then loaded onto a silica gel column and eluted with 1.2:1 dichloromethane: ethyl acetate to afford the title compound (0.45 g, 1.37 mmol) as a yellow solid in 69% yield.

Workup

  1. customThe reaction mixture was purged with H2
  2. filtrationThe palladium was filtered
  3. customthe volatile components were removed in vacuo
  4. dissolutionThe resulting residue was dissolved in methanol
  5. washeluted with 1.2:1 dichloromethane

Sources & evidence

ORD record
ord-22d5f35811d64239b5e9e342a8dbe00b
Source dataset
uspto-grants-2005_11
Patent number
US06967198B2

Reaction notes

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