Hydrochloric Acid → HCID 58368734, compound

HRID 60093Notes

Reaction equation

HRID 60093 reaction equation
[NH2:1][C:2]1[C:3]([F:20])=[C:4]([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([Br:19])[CH:17]=3)[NH:12][CH:11]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34](Cl)(=[O:36])=[O:35].Cl>O1CCCC1>[Br:19][C:16]1[CH:17]=[C:18]2[C:10]([C:8]([C:4]3[C:3]([F:20])=[C:2]([NH:1][S:34]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[F:27])(=[O:36])=[O:35])[CH:7]=[CH:6][CH:5]=3)=[O:9])=[CH:11][NH:12][C:13]2=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 58368906(3-Amino-2-fluoro-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

Product 1

HCID 58368734HCID 58368734, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (3-amino-2-fluoro-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (19, 53 mg, 0.159 mmol) in 0.63 mL of tetrahydrofuran, pyridine (0.115 mL, 1.43 mmol) is added, followed by 2-fluorobenzenesulfonyl chloride (20, 46 mg, 0.238 mmol) and the reaction is stirred at room temperature for 48 hours. Hydrochloric acid (1M aqueous) is added to adjust the mixture to pH 4, and the mixture is extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (21, 56 mg).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated under vacuum
  6. customThe resulting material is purified by silica gel column chromatography
  7. washeluting with ethyl acetate and dichloromethane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ba7ceb1933c64dd387f17d429781fba7
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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