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Methanol → Methyl 6-(cyclopropylmethoxy)-5-fluoronicotinate

HRID 2277168
ノート
印刷プレビュー

反応式

HRID 2277168 の反応式
Br[C:2]1[CH:3]=[C:4]([F:13])[C:5]([O:8][CH2:9][CH:10]2[CH2:12][CH2:11]2)=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:21][OH:22].CN([CH:26]=[O:27])C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl.O>[CH:10]1([CH2:9][O:8][C:5]2[C:4]([F:13])=[CH:3][C:2]([C:21]([O:27][CH3:26])=[O:22])=[CH:7][N:6]=2)[CH2:12][CH2:11]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 867151175-Bromo-2-(cyclopropylmethoxy)-3-fluoropyridine

生成物 1

HCID 86731223Methyl 6-(cyclopropylmethoxy)-5-fluoronicotinate

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物
触媒
HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of 5-bromo-2-(cyclopropylmethoxy)-3-fluoropyridine (2.49 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (832 mg), triethylamine (2.82 mL), methanol (2 mL) and DMF (20 mL) was stirred overnight at 80° C. under a carbon monoxide atmosphere. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.75 g).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-42e0d4e0829042b6aa5359161b811fac
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133129B2

反応ノート

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