Benzophenone imine → HCID 86624015, compound

HRID 643866Notes

Reaction equation

HRID 643866 reaction equation
[CH2:1]([O:8][C:9]1[C:10](Br)=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:14][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](=[NH:41])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C[O-].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[C:28](=[N:41][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:16]=2)[CH:11]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 10942334Sodium MethoxideHCID 66750509HCID 66750509, compound

Product 1

HCID 86624015HCID 86624015, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

3,6-Bis-benzyloxy-2-bromo-naphthalene (2.47 g, 5.89 mmol), benzophenone imine (1.19 mL, 7.07), Pd2(dba)3 (0.013 g, 0.015 mmol), BINAP (0.027 g, 0.044 mmol) and sodium methoxide (0.445 g, 8.25 mmol) are added to a dry flask over nitrogen. Toluene (10 mL) is added at ambient temperature and the reaction heated to 110° C. for 15 h. The reaction mixture is poured into water and extracted with ethyl acetate. The organic layer is dried and evaporated to afford a brown oil, which is chromatographed over silica, eluting with a gradient of 100:1 to 20:1 hexanes/MTBE, to afford benzhydrylidene-(3,6-bis-benzyloxynaphthalen-2-yl)-amine.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer is dried
  3. customevaporated
  4. customto afford a brown oil, which
  5. customis chromatographed over silica
  6. washeluting with a gradient of 100:1 to 20:1 hexanes/MTBE

Sources & evidence

ORD record
ord-357e12c1451c45a78a29835fd67afa5c
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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