2-Methoxyethylamine → 6-Bromo-N-(2-methoxyethyl)-3-pyridinemethanamine

HRID 84386노트

반응식

HRID 84386 반응식
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][CH:3]=1.[CH3:10][O:11][CH2:12][CH2:13][NH2:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[Cl-]>C(Cl)Cl.O>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:14][CH2:13][CH2:12][O:11][CH3:10])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 80182-MethoxyethylamineHCID 25517Ammonium ChlorideHCID 5049666Sodium triacetoxyborohydrideHCID 117692346-Bromo-3-pyridinecarboxaldehyde

생성물 1

HCID 579194786-Bromo-N-(2-methoxyethyl)-3-pyridinemethanamine수율 45%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 6-bromopyridine-3-carbaldehyde (5 g, 26.9 mmol) in DCM (40 mL). was added 2-methoxyethylamine (2.80 mL, 32.3 mmol). After 10 min, sodium triacetoxyborohydride (7.98 g, 37.6 mmol) was added to the mixture and it was stirred at r.t for 17 h. DCM (100 mL water (50 mL and NH4Cl (50 mL) were added to the reaction mixture. The organic phase was collected and the aqueous layer was extracted with DCM (3×100 mL). The combined organic solutions were washed with brine and concentrated under reduce pressure. The residue was purified by flash column chromatography, eluent 98/2 to 95/5 DCM/MeOH, to afford title 143 (2.958 g, 45% yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.31 (dd, J=2.6, 0.6 Hz, 1H), 7.70 (dd, J=8.2, 2.6 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 3.69 (s, 2H), 3.37 (t, J=5.8 Hz, 2H), 3.22 (s, 3H), 2.60 (t, J=5.8 Hz, 2H). MS (m/z): 245.1 (M+H).

후처리

  1. customThe organic phase was collected
  2. extractionthe aqueous layer was extracted with DCM (3×100 mL)
  3. washThe combined organic solutions were washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography, eluent 98/2 to 95/5 DCM/MeOH

출처 및 근거

ORD 기록
ord-c81a356c66964500bc6db0f6b6cf2f42
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846927B2

반응 노트

불러오는 중…