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Diisopropylethylamine → Thiophene-3-carboxylic acid n'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-n'-isopropyl-hydrazid

HRID 2250891
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HRID 2250891 반응식
[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[CH:25]=[CH:24][S:23][CH:22]=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[CH:25]=[CH:24][S:23][CH:22]=1)=[O:20])=[O:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 3028732-(2-Bromo-4-fluorophenoxy)acetic acidHCID 2733179PyBroPHCID 59642162thiophene-3-carboxylic acid N'-isopropyl-hydrazide

생성물 1

HCID 58689906Thiophene-3-carboxylic acid n'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-n'-isopropyl-hydrazid수율 66.4%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

A solution of (2-bromo-4-fluoro-phenoxy)-acetic acid (226 mg, 0.91 mmol) and thiophene-3-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 30-50% ethyl acetate/hexanes gradient to afford the product as a solid (251 mg, 66%).

후처리

  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 30-50% ethyl acetate/hexanes gradient

출처 및 근거

ORD 기록
ord-e9aae6b215af4c9198b145a55baffc76
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07317125B2

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