Sodium bis(trimethylsilyl)amide → N-(5-tert-Butyl-2-methylphenyl)-1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-amine

HRID 1802458노트

반응식

HRID 1802458 반응식
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[N:6]=[C:7]2Cl.[C:18]([C:22]1[CH:23]=[CH:24][C:25]([CH3:29])=[C:26]([CH:28]=1)[NH2:27])([CH3:21])([CH3:20])[CH3:19].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CC(N(C)C)=O>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([CH3:29])=[C:26]([NH:27][C:7]2[C:8]3[C:3](=[C:2]([Cl:1])[N:11]=[CH:10][CH:9]=3)[C:4]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=3[N:6]=2)[CH:28]=1)([CH3:21])([CH3:20])[CH3:19]

참가 물질

5

반응물 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 130899795-tert-Butyl-2-methylanilineHCID 594361181,5-Dichloro-9-fluorobenzo[c]-2,6-naphthyridine

생성물 1

HCID 59436103N-(5-tert-Butyl-2-methylphenyl)-1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-amine

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

To a solution of 1,5-dichloro-9-fluorobenzo[c]-2,6-naphthyridin (Example 1, Step 5) (150 mg, 0.56 mmol) and 5-tert-butyl-2-methylaniline (101 mg, 0.62 mmol) in DMA (2.8 mL) was added NaHMDS (1 M in THF, 1.2 mL, 1.2 mmol) at 0° C. After stirring for 45 minutes, the reaction was quenched by the addition of sat. aq. NaHCO3. The reaction was then extracted with EtOAc and water. The organic extracts were dried over MgSO4 and concentrated in vacuo. Column chromatography on silica gel (100% hexane to 100% EtOAc) provided the title compound.

후처리

  1. customthe reaction was quenched by the addition of sat. aq. NaHCO3
  2. extractionThe reaction was then extracted with EtOAc and water
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-aa07f1c68b7943aaaca920a6691bb40b
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349865B2

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