Dichloromethane → tert-Butyl methyl 5-(5-methylpyridin-2-yl)isophthalate

HRID 888375ノート

反応式

HRID 888375 の反応式
Br[C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[Br-].[CH3:20][C:21]1[CH:22]=[CH:23][C:24]([Zn+])=[N:25][CH:26]=1.[K+].[K+].[K+].C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC([O-])=O.ClCCl>O1CCCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:20][C:21]1[CH:22]=[CH:23][C:24]([C:2]2[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([CH:14]=2)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[N:25][CH:26]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 62717Edetate TripotassiumHCID 66896065Tert-butyl methyl 5-bromoisophthalateHCID 178427808HCID 178427808、化合物

生成物 1

HCID 68499855tert-Butyl methyl 5-(5-methylpyridin-2-yl)isophthalate

試薬・触媒・溶媒 2

HCID 178418851HCID 178418851、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of tert-butyl methyl 5-bromoisophthalate (10.6 g, 33.6 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.31 g, 0.61 mmol) in tetrahydrofuran (160 mL) was added 5-methyl-2-pyridylzinc bromide (0.5 M in THF; 121 mL, 60.5 mmol). The reaction mixture was heated to 60° C. After 18 h, the reaction was cooled to ambient temperature. Aqueous ethylenediaminetetraacetic acid tripotassium salt (0.4 M, 100 mL) and dichloromethane (100 mL) were added. The mixture was stirred for 15 min and the organic solvent was evaporated. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (99% hexanes/ethyl acetate→50% hexanes/ethyl acetate) gave the title compound. MS 328.1 (M+1).

後処理

  1. temperaturethe reaction was cooled to ambient temperature
  2. customthe organic solvent was evaporated
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (99% hexanes/ethyl acetate→50% hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-11bf9e874481447b84115655bc675d74
出典データセット
uspto-grants-2012_08
特許番号
US08247401B2

反応ノート

読み込み中…