4-Methoxybenzylamine → HCID 86659867, compound

HRID 2360138Notes

Reaction equation

HRID 2360138 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)C(C)C)(C)C.[CH3:39][O:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][NH2:46])=[CH:43][CH:42]=1>ClCCl.CCCCCC.Cl>[CH3:39][O:40][C:41]1[CH:48]=[CH:47][C:44]([CH2:45][NH:46][C:19](=[O:21])[O:17][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10]3)=[CH:43][CH:42]=1

Participants

8

Reactant 4

HCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 866598571-Benzylindolin-5-ol

Product 1

HCID 86659867HCID 86659867, compoundYield 68.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1-benzylindolin-5-ol (15.0 mg, 66.6 μmol) in 0.50 mL of dry dichloromethane was added triphosgene (6.9 mg, 23 μmol) and N,N-diisopropylethylamine (14 μL, 82 μmol), successively. After the reaction mixture was stirred at room temperature for 10 min, 4-methoxybenzylamine (17 μL, 0.13 mmol) was added. After the reaction mixture was stirred at the same temperature for 30 min, the reaction mixture was diluted with hexane (1 mL) and 1 M HCl (2 mL). The organic layer was purified directly by silica gel column chromatography (eluting with hexane/ethyl acetate or chloroform/methanol) to obtain the title compound as a white solid (6.1 mg, 24%).

Workup

  1. stirringAfter the reaction mixture was stirred at the same temperature for 30 min
  2. customThe organic layer was purified directly by silica gel column chromatography (eluting with hexane/ethyl acetate or chloroform/methanol)

Sources & evidence

ORD record
ord-3550046c49c54e6b897e262750302c98
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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