Potassium Phosphate, Tribasic → tert-butyl {[4-benzyl-1-(3-methoxypropyl)-1H-indol-3-yl]methyl}cyclopropylcarbamate

HRID 872033Notes

Reaction equation

HRID 872033 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].B1(CC2C=CC=CC=2)C2CCCC1CCC2.C1(P(C2CCCCC2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:38]2[C:43](OC)=[CH:42][CH:41]=[CH:40][C:39]=2OC)CCCCC1.BrC1C=CC=C2[C:56]=1[C:57]([CH2:69][N:70]([CH:78]1[CH2:80][CH2:79]1)[C:71](=[O:77])[O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[CH:58][N:59]2[CH2:64][CH2:65][CH2:66][O:67][CH3:68]>CN(C)C=O.C(OCC)(=O)C.O1CCCC1>[CH2:33]([C:34]1[CH:35]=[CH:36][CH:37]=[C:32]2[C:56]=1[C:57]([CH2:69][N:70]([CH:78]1[CH2:79][CH2:80]1)[C:71](=[O:77])[O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[CH:58][N:59]2[CH2:64][CH2:65][CH2:66][O:67][CH3:68])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 41509249-Benzyl-9-borabicyclo(3.3.1)nonaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86645632tert-butyl {[4-bromo-1-(3-methoxypropyl)-1H-indol-3-yl]methyl}cyclopropylcarbamate

Product 1

HCID 59494459tert-butyl {[4-benzyl-1-(3-methoxypropyl)-1H-indol-3-yl]methyl}cyclopropylcarbamateYield 499.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Potassium phosphate (498 mg), a 0.5M tetrahydrofuran-solution of B-benzyl-9-BBN (2.8 ml), palladium acetate(II) (21 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (38.5 mg) were added to a solution of tert-butyl {[4-bromo-1-(3-methoxypropyl)-1H-indol-3-yl]methyl}cyclopropylcarbamate (205 mg) in N,N-dimethylformamide (4.3 ml) and the mixture was stirred under argon atmosphere at 80° C. for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine successively, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=20/1 to 2/1) to give tert-butyl {[4-benzyl-1-(3-methoxypropyl)-1H-indol-3-yl]methyl}cyclopropylcarbamate (210 mg) as a yellow oil.

Workup

  1. washwashed with water and saturated brine successively
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=20/1 to 2/1)

Sources & evidence

ORD record
ord-1caa458c96fe4315a8c0783c0fc49078
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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