1,4-Dioxane → 5-[3-(ethylsulfonyl)phenyl]-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8H-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

HRID 2060911Notes

Reaction equation

HRID 2060911 reaction equation
I[C:2]1[C:7]2[C:8]3[C:9]([NH:15][C:6]=2[C:5](=[O:16])[N:4]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH:3]=1)=[N:10][CH:11]=[C:12]([CH3:14])[CH:13]=3.[CH2:26]([S:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)(=[O:30])=[O:29])[CH3:27].O1CCOCC1>C(Cl)Cl>[CH2:26]([S:28]([C:31]1[CH:36]=[C:35]([C:2]2[C:7]3[C:8]4[C:9]([NH:15][C:6]=3[C:5](=[O:16])[N:4]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:3]=2)=[N:10][CH:11]=[C:12]([CH3:14])[CH:13]=4)[CH:34]=[CH:33][CH:32]=1)(=[O:29])=[O:30])[CH3:27]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 164271023-Ethylsulfonylphenylboronic acidHCID 588800935-Iodo-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8h-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

Product 1

HCID 588800415-[3-(ethylsulfonyl)phenyl]-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8H-pyrido [4',3':4,5]pyrrolo[2,3-b]pyridin-8-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

In an appropriate microwave reaction vessel was placed, 5-iodo-7-(4-methoxybenzyl)-3-methyl-7,9-dihydro-8H-pyrido[4′,3′:4,5]pyrrolo[2,3-b]pyridin-8-one (8.0 g, 17.967 mmol), 3-(ethylsulfonyl)phenyl boronic acid (4.62 g, 21.6 mmol), and Tetrakis(triphenylphosphine)Pd(0) (6.23 g, 5.4 mmol). The solids were then suspended in a dioxane/saturated K2CO3 solution (40.0 mL, 4/1) and the mixture was heated in a large scale CEM microwave for 20 minutes at 150° C. The reaction mixture was diluted with DCM (400 mL), then filtered off undissolved solids. The organic layer was washed with brine (300 mL), dried with MgSO4, filtered and concentrated in vacuo affording an orange solid. The crude solid was washed with a hot ethyl acetate/hexanes solution (400 mL, 1/1) followed by a hot ethanol/DCM solution (400 mL, 4/1). The product was isolated by filtration, washed with ether and dried under vacuum affording an off-white solid. (6.83 g, 78%) 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36 (t, J=7.45 Hz, 3H) 2.44 (s, 3H) 3.20 (q, J=7.33 Hz, 2H) 3.80 (s, 3H) 5.37 (s, 2H) 6.90 (d, J=8.59 Hz, 2H) 7.16 (s, 1H) 7.37 (d, J=8.59 Hz, 3H) 7.75 (t, J=7.71 Hz, 1H) 7.78-7.87 (m, 2H) 8.03 (d, J=7.58 Hz, 1H) 8.12 (s, 1H) 8.43 (s, 1H). ESI-MS: m/z 488.3 (M+H)+.

Workup

  1. customIn an appropriate microwave reaction vessel
  2. filtrationfiltered off undissolved solids
  3. washThe organic layer was washed with brine (300 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customaffording an orange solid
  8. washThe crude solid was washed with a hot ethyl acetate/hexanes solution (400 mL, 1/1)
  9. customThe product was isolated by filtration
  10. washwashed with ether
  11. customdried under vacuum
  12. customaffording an off-white solid

Sources & evidence

ORD record
ord-464983ed0a3843cb9321424a13e2cd8b
Source dataset
uspto-grants-2012_10
Patent number
US08278450B2

Reaction notes

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