Triethylamine → 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide

HRID 661683노트

반응식

HRID 661683 반응식
[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:44]([C:46]1[CH:53]=[CH:52][CH:51]=[CH:50][C:47]=1[NH:48][CH3:49])[CH3:45]>O.ClCCl>[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([N:48]([C:47]1[CH:50]=[CH:51][CH:52]=[CH:53][C:46]=1[O:44][CH3:45])[CH3:49])=[O:9]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 27595792-Methoxy-N-methylanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110213535-Bromo-4-chloro-2-hydroxybenzoic acid

생성물 1

HCID 686025845-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide수율 10.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a stirring dichloromethane (40 mL) solution containing 5-bromo-4-chloro-2-hydroxybenzoic acid (2.0 g, 8.0 mmol), were added triethylamine (2.2 mL, 16.0 mmol), HATU (4.5 g, 12 mmol) and 2-methoxyl-N-methylaniline (1.19 g, 8.7 mmol). The mixture was stirred at rt for 16 hrs and water was added. The organic layer was separated, washed with NaHCO3, dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash column chromatography eluting with 20% ethyl acetate in hexane to afford 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide (300 mg). MS [M+H]+: 371.9; tR=2.60 min (method 1)

후처리

  1. customThe organic layer was separated
  2. washwashed with NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel flash column chromatography
  7. washeluting with 20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-ec81a83f1b3e488c8193b36c6339b2cc
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084614B2

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