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Water → Ethyl 3-chloro-2-methylisonicotinate

HRID 1508202
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HRID 1508202 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 46311339Ethyl 2,3-dichloropyridine-4-carboxylate

생성물 1

HCID 86721905Ethyl 3-chloro-2-methylisonicotinate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물
촉매
HCID 312751,4-Dioxane용매

실험 절차

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;

후처리

  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)

출처 및 근거

ORD 기록
ord-eff0175657f346fc9430896d99cce9be
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221832B2

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