Potassium Carbonate → 2-Methylpyridine-3-carbonitrile

HRID 7153

반응식

HRID 7153 반응식
[C:1]([C:3]1[C:4](Cl)=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[CH3:10]B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:3]1[C:4]([CH3:10])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 810792-ChloronicotinonitrileHCID 139377Methylboronic Acid

생성물 1

HCID 47383082-Methylpyridine-3-carbonitrile수율 46.1%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a mixture of 3-cyano-2-chloro-pyridine (422 mg, 3.05 mmol), methylboronic acid (209 mg, 3.49 mmol) and K2CO3 (1.22 g, 8.83 mmol) in degassed dioxane (5 mL) under argon was added Pd(PPh3)4 (222 mg, 0.19 mmol) and the mixture stirred at reflux over the weekend. The reaction was cooled to room temperature, diluted with CH2Cl2 (20 mL) and filtered through Celite, washing the cake with CH2Cl2 and MeOH. The filtrate was concentrated in vacuo and purified by column chromatography on silica gel (Hexanes/ethyl acetate, 9:1 then 4:1) to afford the desired product (166 mg, 46%) as a white solid. 1H NMR (CDCl3): δ 2.78 (s, 3H), 7.25 (dd, 1H, J=9, 6 Hz), 7.90 (dd, 1H, J=6, 3 Hz), 8.69 (d, 1H, J=3 Hz).

후처리

  1. temperatureat reflux over the weekend
  2. filtrationfiltered through Celite
  3. washwashing the cake with CH2Cl2 and MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by column chromatography on silica gel (Hexanes/ethyl acetate, 9:1

출처 및 근거

ORD 기록
ord-993a754e79ee4cedb82df3462a06dec6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084155B2

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