Sodium Carbonate → 2-Amino-3-methoxypyridine

HRID 538405

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HRID 538405 반응식
[CH3:1][O:2][C:3]1[C:4]([NH2:18])=[N:5][CH:6]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:8]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:1][O:2][C:3]1[C:4]([NH2:18])=[N:5][CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 2

HCID 10340Sodium CarbonateHCID 533980593-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

생성물 1

HCID 99203842-Amino-3-methoxypyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
100 °C

실험 절차

A mixture 4,5-dibromo-2-(4-(trifluoromethyl)phenyl)-1-((2-trimethylsilyl)ethoxy)methyl-1H-imidazole (730 mg, 1.5 mmol) and 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (400 mg, 1.6 mmol; Example 17, Step 3), and 2.0 M aqueous Na2CO3 solution (3 mL, 6.0 mmol) in DME (10 mL) was purged with Ar for 3 min. Pd(PPh3)4 (65 mg, 0.055 mmol) was added the reaction was heated to 100° C. by for 20 h. The reaction was allowed to cool to rt and phases partitioned. The organic portion was separated and concentrated. The resulting residue crude was purified by flash chromatography (SiO2; 80:20-0:100 hexanes-EtOAc) to furnish 640 mg (1.2 mmol, 80%) of 5-(5-bromo-2-(4-trifluoromethyl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)-3-methoxypyridin-2-amine: LCMS (m/z): 545.0 (MH+), tR=1.02 min.

후처리

  1. temperatureto cool to rt
  2. customphases partitioned
  3. customThe organic portion was separated
  4. concentrationconcentrated
  5. customThe resulting residue crude was purified by flash chromatography (SiO2; 80:20-0:100 hexanes-EtOAc)

출처 및 근거

ORD 기록
ord-88d5aa1709c743cb9a37839de5b18ced
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865732B2

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