Quinoline → HCID 18707021, compound

HRID 1422126Notes

Reaction equation

HRID 1422126 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]3[C:13]=1[C:12](C(O)=O)=[CH:11][C:10]3=[C:17]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:23][CH:22]=1)[C:18]=2[CH2:19][CH3:20])(=[O:3])[CH3:2].N1C2C(=CC=CC=2)C=CC=1>[Cu]>[C:1]([NH:4][C:5]1[C:13]2[N:9]3[C:8](=[CH:7][CH:6]=1)[C:18]([CH2:19][CH3:20])=[C:17]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:23][CH:22]=1)[C:10]3=[CH:11][CH:12]=2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7047QuinolineHCID 18706897HCID 18706897, compound

Product 1

HCID 18707021HCID 18707021, compound

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 7-acetylamino-3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1-carboxylic acid, copper powder (0.52 g), and 130 ml of freshly purified quinoline was heated to 200 ° C. for 2 hours in a nitrogen atmosphere. The copper catalyst was filtered off from the warm mixture. Ice (200 g) was added to the filtrates and the pH was adjusted to 1.5 by addition of a 6M hydrochloric acid solution. The resulting mixture was extracted with dichloromethane. The extract was washed with a 1M hydrochloric acid solution (2×300 ml) followed by a saturated sodium hydrogen carbonate solution (2×250 ml). The dried extract (magnesium sulfate) was evaporated and the residue chromatographed over silica gel with toluene/ethyl acetate (2:1) as eluent to yield 1.52 (64%) of the title compound. M.p. 211-13° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.38 (t, 3H), 2.22 (s, 3H), 3.18 (q, 2H), 5.18 (s, 2H), 7.23 (d, 2H), 7.35-7.55 (m, 7H), 7.75 (d, 2H), 8.03 (d, 1H), 8.22 (d, 1H), 10.50 (s, 1H).

Workup

  1. filtrationThe copper catalyst was filtered off from the warm mixture
  2. additionIce (200 g) was added to the filtrates
  3. additionthe pH was adjusted to 1.5 by addition of a 6M hydrochloric acid solution
  4. extractionThe resulting mixture was extracted with dichloromethane
  5. washThe extract was washed with a 1M hydrochloric acid solution (2×300 ml)
  6. extractionThe dried extract (magnesium sulfate)
  7. customwas evaporated
  8. customthe residue chromatographed over silica gel with toluene/ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-a947224e6fb84cf88a36eaa77947ccb5
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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