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Potassium Carbonate → HCID 46311864, 화합물

HRID 1630746
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HRID 1630746 반응식
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C(=O)([O-])[O-].[K+].[K+].Cl[C:47]1[C:52]([NH2:53])=[CH:51][CH:50]=[C:49]([CH3:54])[N:48]=1>CC([O-])=O.CC([O-])=O.[Pd+2].O.C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C:47]2[C:52]([NH2:53])=[CH:51][CH:50]=[C:49]([CH3:54])[N:48]=2)[CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 27344153-Amino-2-chloro-6-picolineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

생성물 1

HCID 46311864HCID 46311864, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate
촉매
HCID 962Water용매
HCID 6342Acetonitrile용매

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온도
78 °C

실험 절차

To a mixture of 3-fluorophenylboronic acid (1.6 g, 12 mmol), S—PHOS (0.304 g, 0.74 mmol), potassium carbonate (3.41 g, 25 mmol), 2-chloro-6-methylpyridin-3-amine 16 (1.3 g, 9.1 mmol), and Pd(OAc)2 (0.085 g, 0.38 mmol) was added acetonitrile (14 mL) and water (9 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 10 min and the reaction mixture was heated to 78° C. After 4 h, the reaction mixture was diluted with EtOAc, washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (10% to 50% EtOAc in hexanes) gave 2-(3-fluorophenyl)-6-methylpyridin-3-amine.

후처리

  1. customThe reaction mixture was degassed
  2. customby bubbling nitrogen through the solution for 10 min
  3. additionthe reaction mixture was diluted with EtOAc
  4. washwashed with brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash column chromatography on silica gel (10% to 50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-bf74b374d36e48aba7bccd73ffa7a023
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08791147B2

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