HCID 22668216, compound → HCID 22668253, compound

HRID 1007653Notes

Reaction equation

HRID 1007653 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:9]([C:21]1[C:22]([Cl:31])=[N:23][C:24]3[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:8]2)=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[C:9]([C:21]1[C:22]([Cl:31])=[N:23][C:24]3[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:8]2

Participants

4

Reactant 1

HCID 22668216HCID 22668216, compound

Product 1

HCID 22668253HCID 22668253, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of tert-butyl 5-azidomethyl)-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate (7-3, 730 mg, 1.68 mmol) in EtOAc (50 mL) and 10% Pd/C (146 mg) was stirred under a hydrogen balloon at 23° C. for 2 h. The catalyst was filtered and washed with EtOAc (50 mL). The combined filtrate was concentrated to provide tert-butyl 5-(aminomethyl)-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate (7-4) as a white foam. 1H NMR (400 MHz, CDCl3) δ 8.27 (d, 1H, J=8 Hz), 8.18 (s, 1H), 8.07 (d, 1H, J=8 Hz), 7.86 (d, 1H, J=8 Hz), 7.78 (t, 1H, J=8 Hz), 7.61 (t, 1H, J=8 Hz), 7.56 (s, 1H), 7.35 (dd, 1H, J=8, 2 Hz), 6.64 (s, 1H), 4.00 (s, 2H), 1.27 (s, 9H).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with EtOAc (50 mL)
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-865c0207de3a4fa59d9e4100b119eccd
Source dataset
uspto-grants-2004_09
Patent number
US06794393B1

Reaction notes

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