tert-Butanol → Tert-butyl 7-chloro-2,6-naphthyridin-3-ylcarbamate

HRID 468898ノート

反応式

HRID 468898 の反応式
[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

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 123414Diphenylphosphoryl azideHCID 866749707-Chloro-2,6-naphthyridine-3-carboxylic acid

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-48feea5f538b4a57a102398199b2ad1b
出典データセット
uspto-grants-2014_01
特許番号
US08623889B2

反応ノート

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