Methylamine → 2-Methoxy-5-(methylaminocarbonyl)phenylboronic acid

HRID 1478239노트

반응식

HRID 1478239 반응식
[B:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7](O)=[O:8])([OH:3])[OH:2].CN.[CH3:17][N:18](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[CH3:14][O:13][C:12]1[CH:11]=[CH:10][C:6]([C:7](=[O:8])[NH:18][CH3:17])=[CH:5][C:4]=1[B:1]([OH:3])[OH:2]

참가 물질

6

반응물 4

HCID 6329MethylamineHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 426145415-Carboxy-2-methoxybenzeneboronic acid

생성물 1

HCID 574973242-Methoxy-5-(methylaminocarbonyl)phenylboronic acid수율 56.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-Borono-4-methoxybenzoic acid (2.5 g, 12.50 mmol) was dissolved in DMF (6 ml) and 12.50 ml methylamine (2 M solution in THF, 25 mmol) was added followed by HATU (4.75 mg, 12.5 mmol) and NMM (1.375, 12.50 mmol). The reaction mixture was stirred at RT for 20 hours and concentrated. The crude material was added to 50 ml water and extracted 3 times with EtOAc. The combined organic phases were dried (Na2SO4), filtered and concentrated. The crude material was triturated in EtOAc and filtered. The residue was purified by chromatography (Silicagel, CH2Cl2/MeOH 95:5) to give 1.92 g (7.11 mmol, 56.9% yield) of the title compound as a colorless solid. LCMS: (M+H)=210; tR=0.50 min (LC-MS 1). TLC: Rf=0.27 (CH2Cl2/MeOH 95:5). HPLC: tR=3.76 min (HPLC 3). 1H-NMR (d6-DMSO, 600.13 MHz) δ ppm 8.29 (bs, 1H), 8.03 (s, 1H), 7.87 (d, 1H), 7.85 (s, 2H) 7.02 (d, 1H), 3.84 (s, 3H), 2.75 (d, 3H).

후처리

  1. concentrationconcentrated
  2. additionThe crude material was added to 50 ml water
  3. extractionextracted 3 times with EtOAc
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was triturated in EtOAc
  8. filtrationfiltered
  9. customThe residue was purified by chromatography (Silicagel, CH2Cl2/MeOH 95:5)

출처 및 근거

ORD 기록
ord-87687641b35449b98adf98e5ebec1704
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403827B2

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