Benzophenone imine → HCID 86671403, compound

HRID 2403308Notes

Reaction equation

HRID 2403308 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[CH3:21].[C:22](=[NH:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[C:23]1([C:22](=[N:35][C:2]2[N:7]=[CH:6][C:5]([CH:8]3[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]3)=[CH:4][C:3]=2[CH3:21])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 86671402HCID 86671402, compound

Product 1

HCID 86671403HCID 86671403, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of tert-butyl (RS)-2-(6-bromo-5-methylpyridin-3-yl)morpholine-4-carboxylate (1.7 g) and benzophenone imine (1.2 ml) in toluene (20 ml) was added sodium tert-butoxide (732 mg). The reaction mixture was purged with argon for 10 min. (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (296 mg) and tris(dibenzylideneacetone)dipalladium(0) (131 mg) were added and the reaction mixture was heated at 100° C. overnight. The reaction mixture was then cooled to room temperature, poured into water and extracted twice with EtOAc. The organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 75% EtOAc in hexanes) to afford tert-butyl (RS)-2-(6-(diphenylmethyleneamino)-5-methylpyridin-3-yl)morpholine-4-carboxylate (1.01 g, 46%) as a yellow foam. MS (ISP): 458.3 ([M+H]+).

Workup

  1. customThe reaction mixture was purged with argon for 10 min. (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (296 mg) and tris(dibenzylideneacetone)dipalladium(0) (131 mg)
  2. additionwere added
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. additionpoured into water
  5. extractionextracted twice with EtOAc
  6. dry with materialThe organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (silica gel; gradient: 0% to 75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-33b49c5979e54d4da4c0b50bdf2b7d8e
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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