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

HRID 552240Notes

Reaction equation

[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

Participants

Conditions

Temperature: 70 °C

Procedure

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. Retention Time (LC, method: ammonium acetate standard): 1.79 min. MS (M+H+): 266

Workup

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

Sources & evidence

ORD record: ord-6d4df6f01e274fd2b974adff39e7fcc9
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951801B2

Reaction notes

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