Aniline → HCID 22988087, compound

HRID 986998Notes

Reaction equation

HRID 986998 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:9]1[CH:39]=[CH:38][C:12]([O:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:36][CH3:37])=[C:21]([C:24]([NH:26][CH2:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[O:25])[CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[NH:1]([C:9]1[CH:39]=[CH:38][C:12]([O:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:36][CH3:37])=[C:21]([C:24]([NH:26][CH2:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[O:25])[CH:22]=3)[N:17]=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 9827293HCID 9827293, compound

Product 1

HCID 22988087HCID 22988087, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Aniline (0.03 ml) was added to a stirred mixture of 4-(4-bromophenoxy)-7-methoxy-N-(3-morpholinopropyl)quinoline-6-carboxamide (0.132 g), caesium carbonate (0.23 g), palladium acetate (0.01 g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.055 g) and toluene (5 ml) and the reaction mixture was stirred and heated to stirred and heated to 100° C. for 16 hours. The mixture was evaporated and the resultant residue was partitioned between ethyl acetate and water. The organic phase was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulphate. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.103 g); NMR Spectrum: (CDCl3) 1.86 (m, 2H), 2.49 (m, 6H), 3.6 (q, 2H), 3.7 (m, 4H), 4.1 (s, 3H), 5.77 (s, 1H), 6.5 (d, 1H), 6.96 (t, 1H), 7.04-7.17 (m, 6H), 7.3 (m, 2H), 7.5 (s, 1H), 8.02 (m, 1H), 8.63 (d, 1H), 9.19 (s, 1H); Mass Spectrum: M+H+ 513.

Workup

  1. temperatureheated
  2. stirringto stirred
  3. customThe mixture was evaporated
  4. customthe resultant residue was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customThe residue was purified by column chromatography on silica using
  8. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-5a19e374b484487f8869ab7ccbb662c7
Source dataset
uspto-grants-2003_10
Patent number
US06630489B1

Reaction notes

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