Triethylamine → HCID 86600244, compound

HRID 2386970Notes

Reaction equation

HRID 2386970 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][C:14]=1[O:28][CH2:29][CH2:30][F:31])[C:5]2=[O:32].C(N(CC)CC)C.[C]=O.[C:42]([O:45][CH2:46][CH3:47])(=[O:44])C>C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:46]([O:45][C:42]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][C:14]=1[O:28][CH2:29][CH2:30][F:31])[C:5]2=[O:32])=[O:44])[CH3:47]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 23151247HCID 23151247, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 86600244HCID 86600244, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 702EthanolSolvent

Procedure

6-bromo-3-{2-fluoroethoxy-4-[3-(1-pyrrolidinyl)propoxy]phenyl}-2-methyl-4(3H)-quinazolinone synthesized in Example 204 (37 mg), palladium(II) acetate (2 mg), dppf (1,1′-bis(diphenylphosphino)ferrocene) (8.2 mg) and triethylamine (22 mg) were mixed in ethanol (5 mL), and the atmosphere in the system was replaced by carbon monoxide. The mixture was then heated under reflux in the carbon monoxide atmosphere for 2 days. Ethyl acetate was added to the reaction liquid, and the solid precipitate was filtered off. The filtrate was concentrated, purified by silica gel thin layer chromatography (chloroform/methanol=10/1), and the title compound (23 mg, 63%) was thus obtained as a light gray solid.

Workup

  1. temperatureThe mixture was then heated
  2. filtrationthe solid precipitate was filtered off
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel thin layer chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-4c79eca8ff9448afb2910717465125b6
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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