Water → Methyl 5-bromo-6-(cyclopropylmethoxy)picolinate

HRID 632143

반응식

HRID 632143 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([OH:15])=[O:14])=[N:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.IC.[C:18](=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[CH3:18][O:14][C:13]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[C:7]([O:8][CH2:9][CH:10]2[CH2:11][CH2:12]2)[N:6]=1)=[O:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 710875435-Bromo-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

생성물 1

HCID 71087286Methyl 5-bromo-6-(cyclopropylmethoxy)picolinate수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-bromo-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid (Example 9 d, 0.4 g, 1.5 mmol), iodomethane (CAN 16519-98-5, 0.42 g, 3 mmol), sodium carbonate (0.16 g, 1.5 mmol) in DMF (10 mL) was stirred overnight at room temperature. Water was poured into the reaction solution and the resulting mixture was extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography (silica gel, 20 g, 5% ethyl acetate in petroleum ether) to yield the title compound (0.2 g, 0.7 mmol, 48%) as white solid; MS (EI): m/e=286.0 [M+H]+.

후처리

  1. customwas stirred overnight at room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate (3×30 mL)
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel, 20 g, 5% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-983252f5a99e4e5fa5c9ea38e8da3c46
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321727B2

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