Lithium Bromide → 1-(6-Benzyl-3-methyl-3-pyridin-2-yl-2,3-dihydro-indol-1-yl)-ethanone

HRID 1475466Notes

Reaction equation

HRID 1475466 reaction equation
[Li+].[Br-].Br[C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:22])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:9][N:10]2[C:13](=[O:15])[CH3:14])=[CH:6][CH:5]=1.[Br-].[CH2:24]([Zn+])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN1C(=O)CCC1.C1COCC1.C(N1C=CN(C(C)C)C1=[Pd-3](Cl)(Cl)C1C(Cl)=CC=CN=1)(C)C>[CH2:24]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH3:22])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:9][N:10]2[C:13](=[O:15])[CH3:14])=[CH:6][CH:5]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 82050Lithium BromideHCID 709816221-(6-Bromo-3-methyl-3-pyridin-2-yl-2,3-dihydro-indol-1-yl)-ethanoneHCID 178419772HCID 178419772, compound

Product 1

HCID 709809451-(6-Benzyl-3-methyl-3-pyridin-2-yl-2,3-dihydro-indol-1-yl)-ethanoneYield 85.2%

Reagents, catalysts & solvents 3

HCID 178456358HCID 178456358, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a degassed solution of LiBr (165 mg, 1.9 mmol) and (1,3-diisopropylimidazol-2-ylidene)(3-chloropyridyl)palladium (II) dichloride (8 mg, 0.012 mmol) in NMP (3 mL) under N2 were added a solution of 1-(6-bromo-3-methyl-3-pyridin-2-yl-2,3-dihydro-indol-1-yl)-ethanone (400 mg, 1.2 mmol) in THF (3 mL) and benzylzinc bromide (0.5 M in THF, 3.8 mL, 1.9 mmol). The reaction mixture was stirred at room temperature for 16 h and then partitioned between brine and EtOAc. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo. Chromatography (50% EtOAc in Petrol) gave the title compound (350 mg) as a colourless gum. MS: [M+H]+=343.

Workup

  1. custompartitioned between brine and EtOAc
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82a482e8541649a4bafabd44540dd23a
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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