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3-Methoxyaniline → N-(3-Methoxyphenyl)-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide

HRID 31403
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HRID 31403 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[B:11]1[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([NH:25][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([B:11]3[O:12][C:13]([CH3:18])([CH3:19])[C:14]([CH3:17])([CH3:16])[O:15]3)[CH:4]=2)[CH:26]=[CH:27][CH:28]=1
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참가 물질

6

반응물 4

HCID 108243-MethoxyanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 160860864-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid2회

생성물 1

HCID 59791522N-(3-Methoxyphenyl)-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide
수율 73.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid (Intermediate 21) (2 g) was dissolved in dimethylformamide (20 ml). To this was added 3-methoxyaniline (0.985 g), di-isopropylethylamine (4 ml) and HATU (3.05 g). The mixture was stirred for 18 hours at room temperature. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (250 ml) and water (50 ml). The organic layer was dried over magnesium sulfate, filtered and removed in vacuo to give the crude material. The product was purified using silica Biotage cartridge (90 g) eluting with 1:4 ethylacetate/cyclohexane to give a white solid (2.06 g, 5.61 mmol).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (250 ml) and water (50 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customremoved in vacuo
  6. customto give the crude material
  7. customThe product was purified
  8. washeluting with 1:4 ethylacetate/cyclohexane

출처 및 근거

ORD 기록
ord-a58ec41693594b04b2cdb07903357de2
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07425555B2

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