3-Methyl-2-(tributylstannyl)pyridine → Methyl 3,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylate

HRID 2175953노트

반응식

HRID 2175953 반응식
Br[C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[CH3:13][C:14]1[C:15]([Sn](CCCC)(CCCC)CCCC)=[N:16][CH:17]=[CH:18][CH:19]=1>C1(C)C=CC=CC=1.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>[CH3:13][C:14]1[C:15]([C:2]2[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=2)=[N:16][CH:17]=[CH:18][CH:19]=1

참가 물질

5

반응물 2

HCID 164270983-Methyl-2-(tributylstannyl)pyridineHCID 90404668Methyl 3-bromo-6-methylpyridine-2-carboxylate

생성물 1

HCID 90412135Methyl 3,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylate수율 18.9%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
150 °C

실험 절차

To the title compound of step B (509 mg, 2.2 mmol) and the title compound of step C (1.1 g, 2.9 mmol) in PhCH3 (6.6 mL) was added Pd(PPh3)4 (225 mg, 0.2 mmol). The reaction was degassed with N2 and heated at 150° C. for 1.5 h using microwave reactor. The reaction was cooled to rt, diluted with H2O and extracted with EtOAc. The organic layer was dried (MgSO4). Purification via silica gel chromatography (0-100% EtOAc in heptane) gave the title compound (101 mg, 18%). MS (ESI) mass calcd. for C14H14N2O2, 242.3; m/z found 243 [M+H]+.

후처리

  1. customThe reaction was degassed with N2
  2. temperatureThe reaction was cooled to rt
  3. additiondiluted with H2O
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customPurification via silica gel chromatography (0-100% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-8354ce1514984632a8d94ed947c04494
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062078B2

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