Triethylamine → HCID 66679520, compound

HRID 1506682Notes

Reaction equation

HRID 1506682 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[C:13](Cl)[CH:14]=[CH:15][C:16]=3[O:19][CH3:20])[N:11]([CH2:22][CH2:23][F:24])[C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C>CO.[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[O:19][CH3:20])[N:11]([CH2:22][CH2:23][F:24])[C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 66679843HCID 66679843, compound

Product 1

HCID 66679520HCID 66679520, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-chloro-9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester (15) (5.3 g, 15.0 mmol) was dissolved in methanol (180 mL) and triethylamine (1.8 g, 18.0 mmol, 2.5 mL) and 10% Pd/C (2 g in methanol (20 mL)) were added. The mixture was placed on the Parr hydrogenator and shaken for 18 h under a hydrogen atmosphere. The reaction was filtered through a pad of celite, washed with methanol and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (300 mL) and washed with 10% aqueous potassium carbonate (200 mL), dried over magnesium sulfate and concentrated in vacuo to give 4.2 g (88%) of 9-(2-Fluoroethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid ethyl ester (16) as a light brown solid. The structure was confirmed by 13C NMR (75 MHz, CDCl3): δC 14.3, 20.6, 21.8, 27.6, 40.3, 43.3 (d, JCF=23 Hz), 54.9, 60.1, 82.0 (d, JCF=165 Hz), 99.8, 102.1, 107.3, 117.2, 121.8, 134.9, 137.6, 153.8, and 176.0.

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. washwashed with methanol
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  5. washwashed with 10% aqueous potassium carbonate (200 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12921650cb234d68b8f215f33054ea4a
Source dataset
uspto-grants-2015_12
Patent number
US09220795B2

Reaction notes

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