Water → 3-(5-Chloro-2-methoxyphenyl)pyridin-4-amine

HRID 634547노트

반응식

HRID 634547 반응식
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14](B(O)O)[CH:15]=1.C([O-])([O-])=O.[K+].[K+].O>C1(C)C=CC=CC=1.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.C(O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([O:19][CH3:20])=[C:12]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[NH2:8])[CH:11]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15165104-Amino-3-iodopyridineHCID 27357515-Chloro-2-methoxyphenylboronic acid

생성물 1

HCID 509670043-(5-Chloro-2-methoxyphenyl)pyridin-4-amine

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

3-iodopyridin-4-amine (2.2 g, 10 mmol), (5-chloro-2-methoxyphenyl)boronic acid (1.86 g, 10 mmol) and, and K2CO3 (4.2 g, 30 mmol) were mixed in 50 mL of toluene, 5 mL of deionized water and 5 mL of ethanol. To the solution was bubbled with nitrogen for 15 min. Pd(PPh3)4 (0.23 g, 0.2 mmol) was then added. The mixture was refluxed overnight under nitrogen. After cooling, the aqueous layer was removed and the organic layer was then concentrated. The residue was then purified by column chromatography using ethyl acetate as the eluent. 2.0 g (85%) of product was collected as the product.

후처리

  1. customTo the solution was bubbled with nitrogen for 15 min
  2. temperatureThe mixture was refluxed overnight under nitrogen
  3. temperatureAfter cooling
  4. customthe aqueous layer was removed
  5. concentrationthe organic layer was then concentrated
  6. customThe residue was then purified by column chromatography
  7. custom2.0 g (85%) of product was collected as the product

출처 및 근거

ORD 기록
ord-638d4d080b8c4ebf93b1589b2afe3f2d
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09324949B2

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