HCID 67254174, compound → HCID 67254528, compound

HRID 511329Notes

Reaction equation

HRID 511329 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](Br)=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[CH:7]2>CO.C(O)(=O)C.C(Cl)Cl.[Pd]>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[CH:7]2

Participants

6

Reactant 1

HCID 67254174HCID 67254174, compound2×

Product 1

HCID 67254528HCID 67254528, compoundYield 23%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalyst2×HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 8-amino-5-bromo-2-methylisoquinolin-1(2H)-one (Compound 123A, 2.83 g, 10.0 mmol) in a mixture of methanol (120 mL) and acetic acid (5 mL) was hydrogenated over 5% Pd/C (500 mg) under pressure for 24 h. Another batch of 5% Pd/C (400 mg) was added to the reaction mixture and the hydrogenation was continued for a further 24 h. TLC (5% MeOH in CH2Cl2) showed the reaction was complete. The catalyst was filtered off and the filtrate was evaporated to dryness to give a residue, which was purified by column chromatography on silica gel (5% MeOH in CH2Cl2) to afford the title compound as a solid (0.40 g, 23%). 1H NMR (CDCl3, 300 MHz): δ=3.50 (s, 3 H), 6.32 (d, J=7.5 Hz, 1 H), 6.48 (br, 2 H), 6.54 (d, J=7.8 Hz, 1 H), 6.67 (d, J=7.8 Hz, 1 H), 6.91 (d, J=7.5 Hz, 1 H), 7.29 (d, J=7.8 Hz, 1 H).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customto give a residue, which
  4. customwas purified by column chromatography on silica gel (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-ba94b5bd83364590b9ebf40581e7e4fa
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

Loading…