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Potassium Phosphate, Tribasic → 5-(4-Chlorophenyl)-2-{[5-(2,3-difluorophenyl)-2-thienyl]methyl}-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714688
ノート
印刷プレビュー

反応式

HRID 714688 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:21][C@H:22]([OH:27])[C:23]([F:26])([F:25])[F:24])[C:10](=[O:20])[N:11]([CH2:13][C:14]3[S:15][C:16](Cl)=[CH:17][CH:18]=3)[N:12]=2)=[CH:4][CH:3]=1.[F:28][C:29]1[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:21][C@H:22]([OH:27])[C:23]([F:26])([F:25])[F:24])[C:10](=[O:20])[N:11]([CH2:13][C:14]3[S:15][C:16]([C:33]4[CH:32]=[CH:31][CH:30]=[C:29]([F:28])[C:34]=4[F:35])=[CH:17][CH:18]=3)[N:12]=2)=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 2734333(2,3-Difluorophenyl)boronic acidHCID 674115935-(4-Chlorophenyl)-2-[(5-chloro-2-thienyl)methyl]-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

生成物 1

HCID 86690919
5-(4-Chlorophenyl)-2-{[5-(2,3-difluorophenyl)-2-thienyl]methyl}-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

Under an atmosphere of argon, 84 mg (0.19 mmol) of the compound from Example 30A and 45 mg (0.29 mmol) of 2,3-difluorophenylboronic acid were dissolved in 2 ml of toluene. 9 mg (0.01 mmol) of tris(dibenzylideneacetone)dipalladium, 8 mg (0.02 mmol) of 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl and 81 mg (0.38 mmol) of potassium phosphate were then added, and under argon the mixture was heated at 110° C. for 14 h. For work-up, the mixture was diluted at RT with 10 ml of ethyl acetate and 10 ml of water, the organic phase was separated off and the aqueous phase was extracted two more times with in each case 10 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 25 mg (24% of theory) of the target compound.

後処理

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase was extracted two more times with in each case 10 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified chromatographically [Method 19]

出典と根拠

ORDレコード
ord-f2b1f71b0e5544d29f480f0fc5ab9250
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09187466B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート