Selectfluor → 4-Chloro-3-fluoro-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2240251Notes

Reaction equation

HRID 2240251 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:9]=[C:10]([Sn](C)(C)C)[C:3]=12.[B-](F)(F)(F)[F:26].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:9]=[C:10]([F:26])[C:3]=12

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 59305031HCID 59305031, compound

Product 1

HCID 497590784-Chloro-3-fluoro-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

488 mg (1.03 mmol) of 4-chloro-1-[(4-methylphenyl)sulfonyl]-3-(trimethylstannyl)-1H-pyrrolo[2,3-b]pyridine are initially charged in 20 ml of anhydrous acetonitrile. 368 mg (1.03 mmol) of Selectfluor® are then added in one portion, and the mixture is allowed to stir at RT overnight. For work-up, the precipitate formed is filtered off with suction and the filtrate is concentrated. The residue is purified by preparative HPLC. The product is a solid.

Workup

  1. customFor work-up, the precipitate formed
  2. filtrationis filtered off with suction
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-ca6030e585c348e1b8eed8cf285edc57
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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