Selectfluor → ethyl 5-bromo-8-carbamoyl-3-fluoro-9H-carbazole-2-carboxylate

HRID 523241Notes

Reaction equation

HRID 523241 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]2[C:3]=1[C:4]1[CH:5]=[CH:6][C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][C:9]=1[NH:10]2.[F:23][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>C1COCC1.CC#N>[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]2[C:3]=1[C:4]1[CH:5]=[C:6]([F:23])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][C:9]=1[NH:10]2

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 59375100ethyl 5-bromo-8-carbamoyl-9H-carbazole-2-carboxylate

Product 1

HCID 117760923ethyl 5-bromo-8-carbamoyl-3-fluoro-9H-carbazole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 5-bromo-8-carbamoyl-9H-carbazole-2-carboxylate [synthesized according to the procedure described in U.S. Pat. No. 8,084,620, Intermediate 48-1] (0.100 g, 0.277 mmol) and 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) [SELECTFLUOR®] (0.100 g, 0.554 mmol) in THF (2 mL) and MeCN (2 mL) was heated at 60° C. overnight. The cooled mixture was filtered and the filtrate was concentrated. The residue was purified using reverse-phase preparative HPLC to give ethyl 5-bromo-8-carbamoyl-3-fluoro-9H-carbazole-2-carboxylate as a tan solid (0.035 g).

Workup

  1. customsynthesized
  2. filtrationThe cooled mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified

Sources & evidence

ORD record
ord-b34648d717b04772969f24aabc45c01c
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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