Triethylamine → HCID 22048462, compound

HRID 1830814Notes

Reaction equation

HRID 1830814 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[CH:6]=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=1.C[N:22]1[C:26]([Sn](CCCC)(CCCC)CCCC)=CN=C1.[C]=[O:41].[CH2:42]([N:44]([CH2:47]C)[CH2:45][CH3:46])C>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>[Cl:20][C:16]1[CH:15]=[C:14]([C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:46]([C:45]4[N:44]([CH3:42])[CH:47]=[N:22][CH:26]=4)=[O:41])[CH:3]=3)[N:8]([CH3:12])[C:7](=[O:13])[CH:6]=2)[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 109156511-Methyl-5-(tri-n-butylstannyl)imidazoleHCID 22048465HCID 22048465, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 22048462HCID 22048462, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (intermediate 28) (0.066 mol), 1-methyl-5-(tributylstannyl)-1H-imidazole (0.121 mol) and Pd(PPh3)4 (0.0066 mol) in triethylamine (23 ml) and dioxane (230 ml) was stirred at 90° C. overnight under a 5 bar pressure of carbon monoxide, then cooled, poured out into ice water and extracted with EtOAc. The mixture was filtered over celite and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated, yielding fraction 1 (organic layer). Celite was washed with CH2Cl2/CH3OH. The solvent was evaporated, yielding fraction 2. Fraction 2 was washed with diethyl ether, filtered off and dried under a vacuo, yielding 17.6 g (70%) of 4-(3-chlorophenyl)-1-methyl-6-[(1-methyl-1H-imidazol-5-yl)carbonyl]-2(1H)-quinolinone (intermediate 29).

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc
  3. filtrationThe mixture was filtered over celite
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customyielding fraction 1 (organic layer)
  10. washCelite was washed with CH2Cl2/CH3OH
  11. customThe solvent was evaporated
  12. customyielding fraction 2
  13. washFraction 2 was washed with diethyl ether
  14. filtrationfiltered off
  15. customdried under a vacuo

Sources & evidence

ORD record
ord-a94958b5fac842be8ee8452f0f33cc1f
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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