Dichloromethane → HCID 58269152, compound

HRID 1476191Notes

Reaction equation

HRID 1476191 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][C:12]1[O:13][C:14]2[C:19]([C:20](=[O:28])[C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:18][C:17](Br)=[CH:16][CH:15]=2.[H][H].ClCCl>CO.[Pd]>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][C:12]1[O:13][C:14]2[C:19]([C:20](=[O:28])[C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 52911990HCID 52911990, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58269152HCID 58269152, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example 1 (0.1 g, 0.22 mmoles) in methanol (10 ml), palladium on carbon (10 mg) was added and the solution was hydrogenated at RT under 5 kg/cm2 pressure of hydrogen for 3 h. The solution was filtered through celite and concentrated. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as pale yellow solid (0.030 g, 37% yield). MP: 173-175° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 8.10(d, J=12.5Hz, 1H), 8.05(d, J=8.0 Hz, 1H), 7.77 (t, J=7.7 Hz, 1H), 7.48-7.41(m, 6H), 7.22(s,2H), 5.34(s, 2H). Mass: 370.05(M++1).

Workup

  1. filtrationThe solution was filtered through celite
  2. concentrationconcentrated
  3. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-0f858f4c39c74ad8acf67682ce2a9d9a
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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