Toluene → HCID 11294580, compound

HRID 1794998Notes

Reaction equation

HRID 1794998 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[F:23][C:24]([F:51])([F:50])[C:25]1[CH:26]=[C:27]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[CH2:28][N:29]1[CH2:36][CH2:35][CH2:34][O:33][C:32]2[N:37]=[CH:38][CH:39]=[C:40](I)[C:31]=2[C:30]1=[O:42]>C(OCC)(=O)C.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.O1CCOCC1>[F:23][C:24]([F:51])([F:50])[C:25]1[CH:26]=[C:27]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[CH2:28][N:29]1[CH2:36][CH2:35][CH2:34][O:33][C:32]2[N:37]=[CH:38][CH:39]=[C:40]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:31]=2[C:30]1=[O:42]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 114780954-Iodo-6-[3,5-bis(trifluoromethyl)benzyl]-6,7,8,9-tetrahydro-5H-10-oxa-1,6-diazabenzocyclooctene-5-one

Product 1

HCID 11294580HCID 11294580, compoundYield 80.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Phenylboronic acid (417 mg), tetrakis(triphenylphosphine)palladium (132 mg), toluene (10 mL), 1,4-dioxane (5 mL), and a 2 mol/L aqueous solution of sodium carbonate (10 mL) were added to 5-[3,5-bis(trifluoromethyl)benzyl]-7-iodo6-oxo-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (compound of Reference Example 3; 1.00 g). While heated, the mixture was stirred for 7 hours under a stream of argon gas. The reaction mixture was diluted with ethyl acetate, and the diluted mixture was washed with a 2 mol/L aqueous solution of sodium carbonate, and was then dried on anhydrous sodium sulfate. The solvent was removed by distillation to obtain a residue, and then the residue was recrystallized from isopropanol to obtain 5-[3,5-bis(trifluoromethyl)benzyl]-6-oxo-7-phenyl-2,3,4,5-tetrahydro-6H-pyrido[2,3-b][1,5]oxazocine (729 mg, 80%).

Workup

  1. temperatureWhile heated
  2. washthe diluted mixture was washed with a 2 mol/L aqueous solution of sodium carbonate
  3. dry with materialwas then dried on anhydrous sodium sulfate
  4. customThe solvent was removed by distillation
  5. customto obtain a residue
  6. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-1f9ab8b83f6b438a8d98cb69959cc5e1
Source dataset
uspto-grants-2006_04
Patent number
US07026309B2

Reaction notes

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