Piperazine → 8-Piperazin-1-yl-[1,6]-naphthyridine

HRID 428546

反応式

HRID 428546 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CC(C)([O-])C.[Na+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>O>[N:12]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

参加物

6

反応物 4

HCID 4837PiperazineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 8172708-Bromo-1,6-naphthyridineHCID 23676156Sodium t-butoxide

生成物 1

HCID 184141788-Piperazin-1-yl-[1,6]-naphthyridine収率 35.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

To an oven-dried 100 mL flask under a nitrogen atmosphere was added 8-bromo-[1,6]-naphthyridine (1.3 g, 6.2 mmol), piperazine (3.21 g, 37.3 mmol), and sodium t-butoxide (900 mg, 9.33 mmol). The solids were suspended in anhydrous o-xylenes (40 mL), and Pd(dba) (285 mg, 5 mol %) and P(t-Bu)3 (0.31 mL, 1.24 mmol) were added. The reaction mixture was heated at 120° C. for 3 hours. The cooled reaction mixture was poured into H2O (100 mL) and extracted into EtOAc (1×100 mL) and CH2Cl2 (2×100 mL). The organic fractions were combined, dried over Na2SO4, concentrated, and the resulting oil was chromatographed (10% MeOH/CH2CH2+NH4OH) affording 470 mg (35%) of the title compound as a dark gold oil. An analytical sample was prepared as the HCl salt from EtOAc giving a brown solid: mp decomposes above 200° C. MS(+)APCI m/z 215 [M+H]+.

後処理

  1. customThe cooled reaction mixture
  2. extractionextracted into EtOAc (1×100 mL) and CH2Cl2 (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customthe resulting oil was chromatographed (10% MeOH/CH2CH2+NH4OH)

出典と根拠

ORDレコード
ord-e2d7adbde16a48058f97762430a0f203
出典データセット
uspto-grants-2001_11
特許番号
US06313126B1

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