Potassium Carbonate → 6-(2'-Methoxymethyl-biphenyl-4-yloxymethyl)-pyridine-2-carboxylic acid

HRID 2113036노트

반응식

HRID 2113036 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O.[OH-].[K+]>O.O1CCOCC1>[CH3:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:7]2[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[CH:9][CH:8]=2)=[CH:14][CH:15]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 37594082-(Methoxymethyl)benzeneboronic acidHCID 576433496-(4-Iodo-phenoxymethyl)-pyridine-2-carboxylic acid methyl ester2회

생성물 1

HCID 115085346-(2'-Methoxymethyl-biphenyl-4-yloxymethyl)-pyridine-2-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A first stock solution was prepared consisting of 6-(4-iodo-phenoxymethyl)-pyridine-2-carboxylic acid methyl ester (of intermediate 5; 1.77 g, 4.8 mmol), bis(tri -cyclohexyl-phosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 168 mg, 0.25 mmol), and dioxane (approximately 100 mL). A second stock solution was prepared consisting of potassium carbonate (1.99 g, 14.4 mmol) and water (approximately 10 mL). The solutions were sonicated and degassed by bubbling nitrogen gas through them. 4 mL of the first stock solution and 0.4 mL of the second stock solution were added to a reaction tube containing 2-methoxymethyl-phenylboronic acid (available from Apollo Scientific Ltd., Stockport, UK; 100 mg, 0.6 mmol). The mixture was heated in a microwave oven at 170 degrees for 25 min, and then 1 M KOH solution (1 equivalent) was added and the reaction mixture was heated in the microwave for 10 minutes at 120 degrees, for 10 minutes at 130 degrees, and at 170 degrees for one hour. The reaction mixture was then filtered through a silica column (1 g) and washed with dimethylacetamide (2×1 mL). The solvent was evaporated to give 6-(2′-methoxymethyl-biphenyl-4-yloxymethyl)-pyridine-2-carboxylic acid. Mass spectrum MH+=350.

후처리

  1. customA first stock solution was prepared
  2. customA second stock solution was prepared
  3. customThe solutions were sonicated
  4. customdegassed
  5. customby bubbling nitrogen gas through them
  6. addition4 mL of the first stock solution and 0.4 mL of the second stock solution were added to a reaction tube
  7. temperatureThe mixture was heated in a microwave oven at 170 degrees for 25 min
  8. temperaturethe reaction mixture was heated in the microwave for 10 minutes at 120 degrees, for 10 minutes at 130 degrees
  9. filtrationThe reaction mixture was then filtered through a silica column (1 g)
  10. washwashed with dimethylacetamide (2×1 mL)
  11. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-3bac15ca23db4fb086913eaee43e988e
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524870B2

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