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Diisopropylethylamine → thiophene-2-carboxylic acid N'-[2(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide

HRID 2250890
ノート
印刷プレビュー

反応式

HRID 2250890 の反応式
[Br:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[CH:14]([NH:17][NH:18][C:19]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)=[O:20])([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([N:17]([CH:14]([CH3:16])[CH3:15])[NH:18][C:19]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)=[O:20])=[O:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 3028732-(2-Bromo-4-fluorophenoxy)acetic acidHCID 2733179PyBroPHCID 596421662-Thiophenecarboxylic acid, 2-(1-methylethyl)hydrazide

生成物 1

HCID 58689899thiophene-2-carboxylic acid N'-[2(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide収率 70%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A solution of (2-bromo-4-fluoro-phenoxy)-acetic acid (220 mg, 0.91 mmol) and thiophene-2-carboxylic acid N′-isopropyl-hydrazide (200 mg, 1.09 mmol) in DMF (5 ml) was treated with diisopropylethyl amine (0.40 mL, 2.28 mmol) and PyBroP (636 mg, 1.37 mmol) at room temperature overnight. The reaction mixture was partitioned between 1N HCl and ethyl acetate. The organic layer was washed with brine, then dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 10-50% ethyl acetate/hexanes gradient to afford the product as a solid (263 mg, 70%).

後処理

  1. customThe reaction mixture was partitioned between 1N HCl and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 10-50% ethyl acetate/hexanes gradient

出典と根拠

ORDレコード
ord-80c39d437b03462194b1c2de43311004
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07317125B2

反応ノート

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