Dichloromethane → HCID 58269303, compound

HRID 239645Notes

Reaction equation

HRID 239645 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[CH:11]([C:13]1[O:14][C:15]2[C:20]([C:21](=[O:29])[C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[CH3:12].[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[CH:11]([C:13]1[O:14][C:15]2[C:20]([C:21](=[O:29])[C:22]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:12]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 58269240HCID 58269240, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58269303HCID 58269303, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of example 21 (0.080 g, 0.173 mmoles) in methanol (10 ml), palladium on carbon (10% 16 mg) was added and the solution was hydrogenated at RT under 5 kg/cm2 pressure of hydrogen for 24 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 light yellow solid (0.025 g, 38% yield). MP: 254-257° C. 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 8.46(s, 1H), 8.03(s, 1H), 8.01(d, J=1.6 Hz, 1H), 7.83(dt, J=7.3,1.7 Hz, 1H), 7.65 (d, J=8.2 Hz, 1H), 7.50 (m, 4H), 7.37(dd, J=8.1,1.7 Hz, 1H),7.22(s, 2H), 5.67(q, J=7.3 Hz, 1H),1.89(d, J=7.2 Hz, 3H).). Mass: 384.19(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-f1ce31bd5cee44178fa2fb53b8d871d5
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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