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Water → Ethyl 3-chloro-2-methylisonicotinate

HRID 1508202
ノート
印刷プレビュー

反応式

HRID 1508202 の反応式
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[C:7](Cl)[C:6]=1[Cl:12])[CH3:2].[C:14]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1.O>O1CCOCC1.C1C=CC([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)=CC=1>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH3:14])[C:6]=1[Cl:12])[CH3:2]
参加物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 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 46311339Ethyl 2,3-dichloropyridine-4-carboxylate

生成物 1

HCID 86721905Ethyl 3-chloro-2-methylisonicotinate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物
触媒
HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 2,3-dichloroisonicotinic acid ethyl ester (3.15 mmol), K2CO3 (4.73 mmol) and trimethylboroxine (3.15 mmol) in 4 mL dioxane was degassed with Ar. Then, tetrakis(triphenylphosphine)palladium (0.31 mmol) was added and the mixture was heated to reflux overnight. At RT, the reaction mixture was poured into water and extracted with DCM. The combined organic layers were dried over K2CO3, filtered over a pad of celite and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept/EtOAc (8/2) gives the desired product as brown oil;

後処理

  1. customwas degassed with Ar
  2. temperaturethe mixture was heated
  3. temperatureto reflux overnight
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried over K2CO3
  6. filtrationfiltered over a pad of celite
  7. concentrationconcentrated in vacuo
  8. customPurification by CC (KP-SIL™ from Biotage)

出典と根拠

ORDレコード
ord-eff0175657f346fc9430896d99cce9be
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09221832B2

反応ノート

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