p-Toluenesulfonic acid monohydrate → (S)-2-(4-bromo-8-oxo-6,7,8,10-tetrahydro-3H-oxepino[3,4-e]indazol-7-yl)acetic acid

HRID 132456Notes

Reaction equation

HRID 132456 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][C@@H:14]([CH2:18][C:19]([OH:21])=[O:20])[C:15]([OH:17])=[O:16])[C:5]([CH2:11]O)=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][O:16][C:15](=[O:17])[C@H:14]([CH2:18][C:19]([OH:21])=[O:20])[CH2:13][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59732086(S)-2-((7-bromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinic acid

Product 1

HCID 59732081(S)-2-(4-bromo-8-oxo-6,7,8,10-tetrahydro-3H-oxepino[3,4-e]indazol-7-yl)acetic acidYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(S)-2-((7-Bromo-4-(hydroxymethyl)-1H-indazol-5-yl)methyl)succinic acid (95 mg, 0.266 mmol) was suspended in toluene (15 mL). p-Toluenesulfonic acid monohydrate (3.5 mg, 0.018 mmol) was added to the mixture. Reaction was warmed to reflux and held with stirring for 18 hours. Mixture was concentrated to dryness. Title compound was obtained as tan solid in 99% yield. LCMS (M−H)−=339.0, 337.0.

Workup

  1. customReaction
  2. temperaturewas warmed
  3. temperatureto reflux
  4. concentrationMixture was concentrated to dryness

Sources & evidence

ORD record
ord-7922d22c3ede4e3e9509e4effb10b728
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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