Isopropanol → 4-Isopropoxy-6-methyl-[1,5]naphthyridine-3-carbonitrile

HRID 968714ノート

反応式

HRID 968714 の反応式
[CH:1]([OH:4])([CH3:3])[CH3:2].Cl[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[N:14]=2)[N:9]=[CH:8][C:7]=1[C:17]#[N:18]>C1COCC1>[CH:1]([O:4][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[N:14]=2)[N:9]=[CH:8][C:7]=1[C:17]#[N:18])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 3776IsopropanolHCID 587242971,5-Naphthyridine-3-carbonitrile, 4-chloro-6-methyl-

生成物 1

HCID 587243144-Isopropoxy-6-methyl-[1,5]naphthyridine-3-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

To a 50 mL flask placed with KH (30%, 685 mg, 6.0 mmol, pre-washed with nHex) was added a solution of anhydrous isopropanol (0.76 mL, 10.0 mmol) in anhydrous THF (5 mL) at room temperature under argon. The reaction mixture was cooled to −20° C. 4-chloro-6-methyl-[1,5]naphthyridine-3-carbonitrile (407.0 mg, 2.0 mmol) in THF (8 mL) was added dropwise and the reaction mixture was stirred at −20° C. to r.t for 30 min. The reaction mixture was quenched with sat.NH4Cl and extracted with AcOEt (100 mL×3). The combined organic layers was dried over Na2SO4 and concentrated to give the crude product which was purified by flash column (AcOEt/Hex=1/3˜3/2) to give 4-Isopropoxy-6-methyl-[1,5]naphthyridine-3-carbonitrile as white solid (240.0, 52.8%) which was used in the next step without further purification.

後処理

  1. washTo a 50 mL flask placed with KH (30%, 685 mg, 6.0 mmol, pre-washed with nHex)
  2. customThe reaction mixture was quenched
  3. extractionNH4Cl and extracted with AcOEt (100 mL×3)
  4. dry with materialThe combined organic layers was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customwas purified by flash column (AcOEt/Hex=1/3˜3/2)

出典と根拠

ORDレコード
ord-8ce567da35ee44d6928772475db98fe0
出典データセット
uspto-grants-2007_12
特許番号
US07304074B2

反応ノート

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