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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 720144
Notes
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Reaction equation

HRID 720144 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 23938
Palladium
Catalyst
HCID 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-5e752a020bbb4e4d92fc234806e362df
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07132533B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes