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

HRID 2175953ノート

反応式

HRID 2175953 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
150 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-8354ce1514984632a8d94ed947c04494
出典データセット
uspto-grants-2015_06
特許番号
US09062078B2

反応ノート

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