Methanol → 6-chloro-4-fluoro-8-nitro-9H-beta-carboline

HRID 12236

反応式

HRID 12236 の反応式
[N+:1]([O-:4])([O-])=[O:2].[Na+].[Cl:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]1[CH:14]=[N:13][CH:12]=[C:11]([F:20])[C:10]2=1.CO.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[Cl:6][C:7]1[CH:8]=[C:9]2[C:17](=[C:18]([N+:1]([O-:4])=[O:2])[CH:19]=1)[NH:16][C:15]1[CH:14]=[N:13][CH:12]=[C:11]([F:20])[C:10]2=1

参加物

6

反応物 4

HCID 887MethanolHCID 24268Sodium NitrateHCID 516892Sodium BicarbonateHCID 593375246-Chloro-4-fluoro-9H-beta-carboline

生成物 1

HCID 671659696-chloro-4-fluoro-8-nitro-9H-beta-carboline収率 102.2%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒2 回

反応条件

温度
70 °C

実験手順

Sodium nitrate (1.5 eq, 53 mmol, 4.5 g) was added portionwise to a solution of Intermediate 65 (1.0 eq, 35 mmol, 7.8 g) in trifluoroacetic acid (200 mL) and the resulting mixture heated at 70° C. for 3 h. After cooling to RT the trifluoroacetic acid was removed on a rotary evaporator to afford a crude solid which was suspended in a small volume of methanol and added dropwise to a vigorously stirred mixture of saturated sodium bicarbonate solution (500 mL). The resulting slurry was stirred for 15 min then the precipitated solids were collected by suction filtration, washed with water (300 mL) and then dried in vacuo to afford 6-chloro-4-fluoro-8-nitro-9H-β-carboline (about 9.5 g) which was used in the subsequent step without further purification.

後処理

  1. customwas removed on a rotary evaporator
  2. customto afford a crude solid which
  3. filtrationthe precipitated solids were collected by suction filtration
  4. washwashed with water (300 mL)
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-981b4dc1e0c84bf89a142b850617dd70
出典データセット
uspto-grants-2010_06
特許番号
US07727985B2

関連ノート

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