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

HRID 12236

반응식

HRID 12236 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매2회

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-981b4dc1e0c84bf89a142b850617dd70
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727985B2

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