6-bromo-2-chloroquinoline-4-carbonyl chloride → HCID 86598224, compound

HRID 1678312Notes

Reaction equation

HRID 1678312 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[CH:6]=[C:5]2[C:13](Cl)=[O:14].[NH2:16][C:17]1[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:19][O:20][C:21]=1[CH3:22]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[CH:6]=[C:5]2[C:13]([NH:16][C:17]1[C:18]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:19][O:20][C:21]=1[CH3:22])=[O:14]

Participants

4

Reactant 2

HCID 27355526-bromo-2-chloroquinoline-4-carbonyl chlorideHCID 27475845-Methyl-3-phenyl-4-isoxazolamine

Product 1

HCID 86598224HCID 86598224, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

6-Bromo-2-chloroquinoline-4-carbonyl chloride (500 mg) and 4-amino-5-methyl-3-phenylisoxazole (400 mg) were dissolved in dichlorormethane (15 mL) and pyridine (1 mL). The reaction solution was heated at 70° C. overnight. The white precipitation was collected by filtration, washed with ethyl acetate and dried to give 6-bromo-2-chloro-N-(5-methyl-3-phenylisoxazol-4-yl)-4-quinolinecarboxamide (520 mg) as a white solid. 1H NMR (DMSO-d6): δ 2.52 (s, 3H), 7.52 (m, 3H), 7.72 (m, 2H), 8.02 (m, 4H), 10.58 (s, 1H); LCMS: ret. time: 32.23 min.; purity: 100%; MS (m/e): 441.82 (M+).

Workup

  1. customThe white precipitation
  2. filtrationwas collected by filtration
  3. washwashed with ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-caf792ac3dd04e90b74042c927b33ca2
Source dataset
uspto-grants-2011_08
Patent number
US08008501B2

Reaction notes

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