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

HRID 1802458ノート

反応式

HRID 1802458 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aa07f1c68b7943aaaca920a6691bb40b
出典データセット
uspto-grants-2013_01
特許番号
US08349865B2

反応ノート

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