Diisopropylethylamine → Methyl 5-(3-fluorobenzyl)picolinate

HRID 1777539

반응식

HRID 1777539 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 67974406Methyl 5-(3-fluorobenzyl)picolinate수율 264.2%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-194953a6edf845e894921923b3018298
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266832B2

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