Potassium Carbonate → HCID 90016647, compound

HRID 1484425Notes

Reaction equation

HRID 1484425 reaction equation
[C:1]([N:6]1[CH2:27][CH2:26][C:9]2[N:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]3[CH:12]=[CH:13][C:14](Br)=[CH:15][C:16]=3[C:8]=2[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].[C:28]1([CH3:37])[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([N:6]1[CH2:27][CH2:26][C:9]2[N:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]3[CH:12]=[CH:13][C:14]([C:30]4[CH:29]=[C:28]([CH3:37])[CH:33]=[CH:32][CH:31]=4)=[CH:15][C:16]=3[C:8]=2[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339503-Tolylboronic acidHCID 90024195HCID 90024195, compound

Product 1

HCID 90016647HCID 90016647, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To the mixture of 2-Carbethoxy-8-bromo-5-n-octyl-1,2,3,4-tetrahydropyrido[4,3-b]indole (4b, 1 equiv.), m-tolylboronic acid (1.1 equiv.) and Pd(PPh3)4 (0.05 equiv.) in 12 mL 1,4-dioxane was added 4 mL aqueous solution of K2CO3 (3 equiv.). The mixture was refluxed under N2 atmosphere for about 10 h. On cooling, the solvent was evaporated and the resulting residue was extracted with DCM (20 mL×3), the DCM layer was washed with brine, dried (Na2SO4) and filtered. The residue obtained on removal of the solvent was purified by column chromatography on silica gel with EtOAc/hexane as eluting solvents to give the target compound 2-carbethoxy-8-m-tolyl-5-octyl-1,2,3,4-tetrahydropyrido[4,3-b]indole (7). Yield: 60.4%. 1H NMR (300 Hz, CDCl3) δ 7.67 (br, 1H), 7.48-7.43 (m, 3H), 7.35-7.31 (m, 2H), 7.15-7.12 (m, 1H), 4.76 (s, 2H), 4.22 (q, 2H, J=7.2 Hz), 4.03 (t, 2H, J=7.2 Hz), 3.91 (br, 2H), 2.84 (br, 2H), 2.45 (s, 3H), 1.77-1.73 (m, 2H), 1.35-1.27 (m, 13H), 0.89 (t, 3H, J=6.5 Hz). 13C NMR (75 Hz, CDCl3) δ 156.09, 142.48, 138.10, 135.83, 132.72, 128.50, 128.09, 126.98, 125.57, 124.39, 120.83, 118.99, 116.15, 109.29, 106.70, 61.49, 60.36, 43.21, 41.31, 31.75, 30.38, 29.28, 29.13, 27.04, 22.57, 21.56, 14.73, 14.16, 14.03.

Workup

  1. temperatureThe mixture was refluxed under N2 atmosphere for about 10 h
  2. temperatureOn cooling
  3. customthe solvent was evaporated
  4. extractionthe resulting residue was extracted with DCM (20 mL×3)
  5. washthe DCM layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe residue obtained on removal of the solvent
  9. customwas purified by column chromatography on silica gel with EtOAc/hexane
  10. washas eluting solvents

Sources & evidence

ORD record
ord-b6cca242b930440c9d2bac23eee532a9
Source dataset
uspto-grants-2016_08
Patent number
US09422238B2

Reaction notes

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