叔丁醇 → Tert-butyl 7-chloro-2,6-naphthyridin-3-ylcarbamate

HRID 468898笔记

反应方程式

HRID 468898 反应方程式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7](C(O)=O)[N:8]=[CH:9]2)=[CH:4][N:3]=1.[C:15]([OH:19])([CH3:18])([CH3:17])[CH3:16].C([N:23]([CH2:27]C)C(C)C)(C)C.C1C=CC([O:35]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:23][C:27](=[O:35])[O:19][C:15]([CH3:18])([CH3:17])[CH3:16])[N:8]=[CH:9]2)=[CH:4][N:3]=1

参与物

7

反应物 4

HCID 6386叔丁醇HCID 81531N,N-二异丙基乙胺HCID 123414叠氮磷酸二苯酯HCID 866749707-Chloro-2,6-naphthyridine-3-carboxylic acid

产物 1

HCID 86674971Tert-butyl 7-chloro-2,6-naphthyridin-3-ylcarbamate收率 83%

试剂、催化剂与溶剂 2

HCID 1140甲苯溶剂HCID 8857乙酸乙酯溶剂

反应条件

温度
110 °C

实验过程

A mixture of 7-chloro-2,6-naphthyridine-3-carboxylic acid (360 mg, 1.8 mmol), tert-butyl alcohol (3.4 mL), N,N-diisopropylethylamine (1 mL, 5.6 mmol), and diphenylphosphonic azide (1.0 mL, 4.5 mmol) in toluene (6 mL) was heated at 110° C. for 1 hour. The cooled reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 12 g, ISCO, 0-60% ethyl acetate in heptane) to afford the title compound as a pale yellow solid (410 mg, 83%), which was used in the next step without further purification.

后处理

  1. customThe cooled reaction mixture
  2. washwashed with water (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by flash chromatography (silica, 12 g, ISCO, 0-60% ethyl acetate in heptane)

来源与证据

ORD记录
ord-48feea5f538b4a57a102398199b2ad1b
来源数据集
uspto-grants-2014_01
专利号
US08623889B2

反应笔记

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