Toluene → HCID 178487321, compound

HRID 1749903Notes

Reaction equation

HRID 1749903 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[CH2:8][O:9][C:5]=2[C:4]=1[O:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH:36]=O)=[N:28]1.C1(C)C=CC=CC=1>CO.N1CCCCC1>[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](/[CH:36]=[C:8]2\[O:9][C:5]3[C:4]([O:13][CH:14]4[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]4)=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=3[C:7]\2=[O:10])=[N:28]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 71278776HCID 71278776, compoundHCID 178520025HCID 178520025, compound

Product 1

HCID 178487321HCID 178487321, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yloxy)piperidine-1-carboxylate (0.019 g, 0.052 mmol) in methanol (2.0 mL) was added with 1H-indazole-3-carboxaldehyde (0.008 g, 0.057 mmol). Then, the mixture was added with 5 drops of piperidine, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was added with toluene, the solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate (2:1→1:4)) to obtain tert-butyl (Z)-4-{2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yloxy}piperidine-1-carboxylate (0.020 g, 79%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate (2:1→1:4))

Sources & evidence

ORD record
ord-bfa63a76756f4774989418ad7bd7911b
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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