HCID 67357986, compound → HCID 67359810, compound

HRID 1664491Notes

Reaction equation

HRID 1664491 reaction equation
C([O:8][C:9]([CH:11]1[CH2:23][C:22]2[C:21]3[C:16](=[C:17]([Cl:24])[CH:18]=[CH:19][CH:20]=3)[N:15]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:14]=2[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1>[Pd].C(O)C>[CH2:29]([O:28][C:26]([CH2:25][N:15]1[C:14]2[CH2:13][CH2:12][CH:11]([C:9]([OH:10])=[O:8])[CH2:23][C:22]=2[C:21]2[C:16]1=[C:17]([Cl:24])[CH:18]=[CH:19][CH:20]=2)=[O:27])[CH3:30]

Participants

4

Reactant 1

HCID 67357986HCID 67357986, compound

Product 1

HCID 67359810HCID 67359810, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8-chloro-9-ethoxycarbonylmethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid benzyl ester (2.5 g, 5.9 mmol) and 10% palladium on activated charcoal (480 mg) in ethanol (200 ml) is stirred under a hydrogen atmosphere for 1 h. The catalyst is filtered off and washed with ethanol. The filtrate is concentrated to dryness to deliver Intermediate 1.3. tR (LC-5) 0.96 min; ESI-MS (positive ion): m/z 336.23 [M+H]+ (calcd 335.79 for C17H18NO4C1). 1H-NMR (DMSO-d6): 1.18 (t, J=7.0 Hz, 3H); 1.85 (m, 1H); 2.19 (m, 1H); 2.66 (m, 4H); 2.90 (m, 1H); 4.14 (q, J=7.0 Hz, 2H); 5.17 (s, 2H); 6.96 (t, J=7.6 Hz, 1H); 7.04 (d, J=7.3 Hz, 1H); 7.38 (d, J=7.6 Hz, 1H); 12.3 (br s, 1H).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with ethanol
  3. concentrationThe filtrate is concentrated to dryness
  4. custom0.96 min

Sources & evidence

ORD record
ord-87a6c183a7d94fc28a778ec8ffeec188
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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