Diisopropylethylamine → Methyl 5-(3-fluorobenzyl)picolinate

HRID 1777539

反応式

HRID 1777539 の反応式
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([O:21][CH3:22])=[O:20])=[N:17][CH:18]=1.C(N(CC)C(C)C)(C)C>C(COC)OC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([O:21][CH3:22])=[O:20])=[N:17][CH:18]=1

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 27339863-Fluorophenylboronic acidHCID 19699469Methyl 5-(bromomethyl)pyridine-2-carboxylate

生成物 1

HCID 67974406Methyl 5-(3-fluorobenzyl)picolinate収率 264.2%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 3-fluorophenylboronic acid (0.319 g; 2.28 mmol), methyl 5-(bromomethyl)picolinate (0.350 g; 0.230 mmol), tetrakis-(triphenylphosphine)-palladium(0) (0.175; 0.152 mmol) and N,N diisopropylethylamine (0.524 g; 3.04 mmol) in dimethoxyethane (9 mL) and water (3 mL) was irradiated in a microwave oven at 130° C. for 20 minutes. The resulting solution was partitioned between water and ethyl acetate. The organic layer was separated and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 1 to 10% ethyl acetate in dichlomethane) to afford 0.149 g (40%) of the title compound as a yellow oil.

後処理

  1. customwas irradiated in a microwave oven at 130° C. for 20 minutes
  2. customThe resulting solution was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by flash chromatography on silica gel (eluent 1 to 10% ethyl acetate in dichlomethane)

出典と根拠

ORDレコード
ord-194953a6edf845e894921923b3018298
出典データセット
uspto-grants-2016_02
特許番号
US09266832B2

関連ノート

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