Ethyl 5-bromo-1,3,4,9-tetrahydro-8-methyl-1-propylpyrano[3,4-b]indole-1-acetate → HCID 5273764, compound

HRID 1351719Notes

Reaction equation

HRID 1351719 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1([CH2:21][CH2:22][CH3:23])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[C:17](Br)[CH:16]=[CH:15][C:14]=3[CH3:20])[CH3:2].[C:25]([Cu])#[N:26]>CN1CCCC1=O.O>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1([CH2:21][CH2:22][CH3:23])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[C:17]([C:25]#[N:26])[CH:16]=[CH:15][C:14]=3[CH3:20])[CH3:2]

Participants

5

Reactant 2

HCID 11452194Ethyl 5-bromo-1,3,4,9-tetrahydro-8-methyl-1-propylpyrano[3,4-b]indole-1-acetateHCID 178418546HCID 178418546, compound

Product 1

HCID 5273764HCID 5273764, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
220 °C

Procedure

5-Bromo-8-methyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester (1.27 g, 3.22 mmol) and CuCN (0.433 g, 4.83 mmol) was dissolved in N-methyl-2-pyrrolidinone (15 mL) and the solution was divided into the 4 microwave reaction vessels (3.75 mL each). The reaction vessels were heated in microwave at 220° C. for 15 minutes. The reaction mixtures in 4 vessels were combined and then diluted with water (30 mL). The crude mixture was extracted with EtOAc (3×50 mL). The combined organic phase was washed with brine (100 mL), dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (silica, 20% EtOAc in hexanes) to give 0.959 g (88%) of title compound as a white solid. 1H NMR (CDCl3): 300 MHz δ 9.75 (bs, 1H), 7.33 (d, J=7.52 Hz, 1H), 6.93 (d, J=7.52 Hz, 1H), 4.21 (m, 2H), 4.11 (m, 1H), 4.03 (m, 1H), 3.08 (t, J=5.52, 2H), 2.99 (d, J=4.17 Hz, 2H), 2.57 (s, 3H), 2.06 (m, 2H), 1.42 (m, 1H), 1.26 (t, J=7.16 Hz, 3H), 1.18 (m, 1H), 0.88 (t, J=7.32 Hz, 3H).

Workup

  1. customthe solution was divided into the 4 microwave reaction vessels (3.75 mL each)
  2. customThe reaction vessels
  3. customThe reaction mixtures in 4 vessels
  4. extractionThe crude mixture was extracted with EtOAc (3×50 mL)
  5. washThe combined organic phase was washed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (silica, 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ab7ce99fffda49b698c342ce0db26dc2
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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