Bis[2-(diphenylphosphino)phenyl] ether → 6-[(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)thio]-4-[(3-methoxyphenyl)amino]quinoline-3-carboxamide

HRID 230853ノート

反応式

HRID 230853 の反応式
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([NH:14]C(=O)OC(C)(C)C)=[O:13])=[C:5]2[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1.[Si:31]([O:38][C:39]1[CH:44]=[CH:43][C:42]([SH:45])=[CH:41][CH:40]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[Si:31]([O:38][C:39]1[CH:44]=[CH:43][C:42]([S:45][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([NH2:14])=[O:13])=[C:5]3[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)=[CH:41][CH:40]=1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

参加物

8

反応物 4

HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 11701480Benzenethiol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-HCID 23665647Potassium tert-butoxideHCID 57763225HCID 57763225、化合物

生成物 1

HCID 577632316-[(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)thio]-4-[(3-methoxyphenyl)amino]quinoline-3-carboxamide収率 46.4%

試薬・触媒・溶媒 3

HCID 9832798Tris(dibenzylideneacetone) dipalladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A stirred mixture of Intermediate 37 (0.8 g) and 4-{[tert-butyl(dimethyl)silyl]oxy} benzenethiol (0.74 g, EP465802A1), with (oxydi-2,1-phenylene)bis(diphenylphosphine) (0.05 g), potassium tert-butoxide (0.26 g) and tris(dibenzylideneacetone) dipalladium(0) (0.08 g) in toluene (30 ml) was heated at 106° C. for 18 h. The mixture was cooled, diluted with ethyl acetate (25 ml) and washed with a sodium carbonate solution (30 ml). The organic extracts were washed with water (30 ml) , dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel using ethyl acetate/diethyl ether (7:3) as the eluent. The appropriate fractions were concentrated in vacuo to give the title compound as a yellow foam (0.38 g).

後処理

  1. temperatureThe mixture was cooled
  2. washwashed with a sodium carbonate solution (30 ml)
  3. washThe organic extracts were washed with water (30 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel
  7. concentrationThe appropriate fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-b6f28e2cc1304101b966e5107ae9d6a1
出典データセット
uspto-grants-2009_07
特許番号
US07566786B2

反応ノート

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