Benzophenone imine → HCID 131733653, compound

HRID 1753044Notes

Reaction equation

HRID 1753044 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[N:12]([CH:19]([CH3:29])[CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1.CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC=2)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+].[C:66](=[NH:79])([C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Si:22]([O:21][CH2:20][C@@H:19]([N:12]1[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[C:10]([C:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([N:79]=[C:66]([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)[CH:3]=2)=[O:9])=[CH:11]1)[CH3:29])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 136809Benzophenone imineHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 23676156Sodium t-butoxideHCID 131733654HCID 131733654, compound

Product 1

HCID 131733653HCID 131733653, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To a solution of (5-bromopyridin-3-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone (Enantiomer 1, Preparation 41, 3.2 g, 0.067 mol) in toluene (90 mL) was added tBuXphos (785 mg, 0.0018 mol), NaOtBu (605 mg, 0.0018 mol), benzophenone imine (1.34 g, 0.0074 mol) and Pd2(dba)3 and the reaction was stirred at room temperature for 18 hours. The reaction was filtered through celite and the filtrate extracted into EtOAc. The organic layer was collected, washed with brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 50% EtOAc in heptanes to afford the title compound (1.3 g, 33%).

Workup

  1. filtrationThe reaction was filtered through celite
  2. extractionthe filtrate extracted into EtOAc
  3. customThe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washeluting with 50% EtOAc in heptanes

Sources & evidence

ORD record
ord-39cc9f37343540e8ad2f856e6ffa6829
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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