Boron tribromide → HCID 59436049、化合物

HRID 1802488ノート

反応式

HRID 1802488 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][N:23]=[C:24]([O:25]CC)[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1.ClC1C2C3C(=CC=NC=3)N=C(NC3C(F)=CC(F)=CC=3Cl)C=2C=CN=1.C[O-].[Na+].B(Br)(Br)Br>CO>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][NH:23][C:24](=[O:25])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1

参加物

6

反応物 4

HCID 25134Boron tribromideHCID 10942334Sodium MethoxideHCID 59436014HCID 59436014、化合物HCID 59436106HCID 59436106、化合物

生成物 1

HCID 59436049HCID 59436049、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

To a solution of N-(2-chloro-4,6-difluorophenyl)-10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-amine and 10-chloro-N-(2-chloro-4,6-difluorophenyl)pyrido[4,3-c]-1,6-naphthyridin-6-amine (1.3 g) in 8 mL methanol was added sodium methoxide (5 mL, 2.06 mmol, 25% weight in methanol) and the mixture was heated to 100° C. for 1 hr. The solution was cooled to room temperature, concentrated, and redissolved with 3:1 CHCl3/i-PrOH followed by a wash with saturated NH4Cl. The organic layers were combined, dried with MgSO4, filtered, and concentrated under reduced pressure. A portion of the crude solution (540 mg) was taken up in CHCl3 (8 mL) and boron tribromide (1M in CH2Cl2, 7 mL, 7.0 mmol) and heated to 85° C. for 1 hr. The solution was cooled to room temperature, extracted with 3:1 CHCl3/i-PrOH, and washed with saturated NaHCO3. The organic layers were dried with MgSO4, filtered, and concentrated to afford the crude product. The crude residue was purified on silica gel (100% CH2Cl2 to 25% MeOH, gradient elution) which afforded the title compound.

後処理

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionredissolved with 3:1 CHCl3/i-PrOH
  4. washa wash with saturated NH4Cl
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. temperatureThe solution was cooled to room temperature
  9. extractionextracted with 3:1 CHCl3/i-PrOH
  10. washwashed with saturated NaHCO3
  11. dry with materialThe organic layers were dried with MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customto afford the crude product
  15. customThe crude residue was purified on silica gel (100% CH2Cl2 to 25% MeOH, gradient elution) which

出典と根拠

ORDレコード
ord-0f8cc2bc16d14e43826db59610443758
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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