Benzophenone imine → 6-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amine

HRID 1748536Notes

Reaction equation

HRID 1748536 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([C:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH:9]=2)=[N:6][CH:7]=1.[C:19](=[NH:32])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:15]1[C:11]2([CH2:16][CH2:17][CH:8]([C:5]3[N:6]=[CH:7][C:2]([N:32]=[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:3][C:4]=3[CH3:18])[CH2:9][CH2:10]2)[O:12][CH2:13][CH2:14]1

Participants

7

Reactant 3

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 866924755-Bromo-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-3-methylpyridine

Product 1

HCID 866924886-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amineYield 93.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

A suspension of 5-bromo-2-(1,4-dioxaspiro[4.5]decan-7-en-8-yl)-3-methylpyridine (22.5 g) in Reference Example 105, benzophenone imine (13.9 g), palladium acetate (204 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (567 mg) and sodium tert-butoxide (10.5 g) in toluene (150 ml) was stirred for 6 hours under heating to reflux. After completion of the reaction, the mixture was allowed to cool, ice water was added thereto, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated to give 6-(1,4-dioxaspiro[4.5]decan-8-yl)-N-(diphenylmethylene)-5-methylpyridin-3-amine (28 g) as a brown oil. MS (ESI) m/z: 411 (M+H)+.

Workup

  1. temperatureunder heating to reflux
  2. customAfter completion of the reaction
  3. temperatureto cool
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d6cfad3138474c5794ace8faea48788e
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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