Hydrochloric Acid → HCID 68008364、化合物

HRID 533161ノート

反応式

HRID 533161 の反応式
Br[C:2]1[CH:3]=[N:4][C:5](Cl)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC.Cl.C(=O)(O)[O-].[Na+].[C:34]1(C)C=CC=C[CH:35]=1>C1(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)C=CC=CC=1>[CH:13]([C:5]1[N:4]=[CH:3][C:2]([CH:34]=[CH2:35])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])=[CH2:14]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 81998TributylvinyltinHCID 516892Sodium BicarbonateHCID 2763343Methyl 5-bromo-2-chloronicotinate

生成物 1

HCID 68008364HCID 68008364、化合物収率 86%

試薬・触媒・溶媒 1

HCID 178420554HCID 178420554、化合物触媒

反応条件

温度
110 °C

実験手順

Methyl 5-bromo-2-chloronicotinate (6.9 g, 27.6 mmol) was dissolved into toluene (100 mL). Tributyl(vinyl)tin (19.7 g, 62.1 mmol) was added, followed by tetrakistriphenylphosphinopalladium (2.5 g, 2.1 mmol), and the reaction heated at 110° C. for 3 h. The reaction mixture was poured onto 2 N HCl (100 mL) and stirred for 30 min, then neutralized with saturated sodium bicarbonate. The organic layer was removed, concentrated and purified over silica gel using automated chromatography to give 4.5 g (86%) of the compound. LC-MS (M+H)=190.1.

後処理

  1. customThe organic layer was removed
  2. concentrationconcentrated
  3. custompurified over silica gel using automated chromatography

出典と根拠

ORDレコード
ord-f821f7e0e89d4d5bbf7211364d9b9990
出典データセット
uspto-grants-2014_10
特許番号
US08853237B2

反応ノート

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