Dimethylformamide → HCID 57531283、化合物

HRID 643479

反応式

HRID 643479 の反応式
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23](Br)[CH:22]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[C:11]([F:20])[CH:10]=2)[N:3]=1.[CH3:29][N:30]([CH3:33])C=O>C1(P([Pd-](Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:9]3[CH:29]=[N:30][CH:33]=[C:11]([F:20])[CH:10]=3)[CH:22]=2)([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[C:11]([F:20])[CH:10]=2)[N:3]=1

参加物

4

反応物 2

HCID 6228DimethylformamideHCID 57531264HCID 57531264、化合物

生成物 1

HCID 57531283HCID 57531283、化合物収率 74%

試薬・触媒・溶媒 1

HCID 178479804HCID 178479804、化合物触媒

反応条件

温度
150 °C

実験手順

A mixture of 2-amino-5-(3-bromo-4-fluorophenyl)-5-[3-fluoro-4-(trifluoromethoxy)phenyl]-3-methyl-3,5-dihydroimidazol-4-one (0.17 g, 0.366 mmol), 5-fluorpyridin-3-yl-tri(n-butyl)stannate (0.212 g, 0.55 mmol) and bis(triphenylphosphino)palladium(II) chloride (0.013 g, 0.018 mmol) in dimethyl formamide is degassed, heated at 150° C. for 1 h, cooled to room temperature and diluted with ethyl acetate and 2% aqueous lithium chloride. The organic phase is separated, washed with 2% aqueous lithium chloride, dried over sodium sulfate and concentrated in vacuo. Purification of the resultant residue by flash chromatography (silica, 97:3:0.25 methylene chloride/methanol/concentrated ammonium hydroxide as eluent) affords the title compound as a white solid, 0.130 g (74% yield), mp 91-97° C.; identified by HNMR and mass spectral analyses. 1H NMR (300 MHz, CD3OD) 8.55 (m, 1H), 8.49 (d, J=3.0 Hz, 1H), 7.83 (d, J=9.6 Hz, 1H), 7.60-7.21 (m, 6H), 3.13 (s, 3H); IR (ATR) 3352, 3070, 1732, 1669, 1598, 2502, 1479, 1421, 1252, 1217, 1171, 883, 817, 794, 703 cm−1; ESI MS m/z 481

後処理

  1. customis degassed
  2. temperaturecooled to room temperature
  3. additiondiluted with ethyl acetate and 2% aqueous lithium chloride
  4. customThe organic phase is separated
  5. washwashed with 2% aqueous lithium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification of the resultant residue by flash chromatography (silica, 97:3:0.25 methylene chloride/methanol/concentrated ammonium hydroxide as eluent)

出典と根拠

ORDレコード
ord-74ac0ada288c423aa6749d1c3be1695c
出典データセット
uspto-grants-2010_04
特許番号
US07700602B2

関連ノート

読み込み中…