4-Bromoaniline → HCID 86602397, compound

HRID 1454928Notes

Reaction equation

HRID 1454928 reaction equation
ClC(OCC(C)C)=O.[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]([OH:20])=O)=[N:10]1.C[N:22]1CCOCC1.[Br:28][C:29]1[CH:35]=[CH:34][C:32](N)=[CH:31][CH:30]=1>C1COCC1>[Br:28][C:29]1[CH:35]=[CH:34][C:32]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]([NH2:22])=[O:20])=[N:10]2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 78074-BromoanilineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 78250Indazole-3-carboxylic acid

Product 1

HCID 86602397HCID 86602397, compoundYield 160.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, isobutyl chloroformate (357 μl, 2.75 mmol) is added at 0° C. to an indazole-3-carboxylic acid solution (405 mg, 2.5 mmol) in THF (50 ml), followed by N-methylmorpholine (302 μl, 2.75 mmol). The reaction mixture is stirred for 15 min at 0° C. and then 4-bromoaniline (860 mg, 5 mmol) is added. The ice bath is removed and the stirring is maintained overnight. The solvent is evaporated under vacuum. The residue is taken up in an AcOEt/H2O mixture. The evaporation of the organic solution after drying over MgSO4 gives a crude compound (1.27 g) which is chromatographed on silica, eluting with CH2Cl2. The compound thus obtained is recrystallized from isopropanol.

Workup

  1. customThe ice bath is removed
  2. temperaturethe stirring is maintained overnight
  3. customThe solvent is evaporated under vacuum
  4. customThe evaporation of the organic solution
  5. dry with materialafter drying over MgSO4

Sources & evidence

ORD record
ord-d124075abe5641dbb0bc3ffc5c27f6e2
Source dataset
uspto-grants-2009_01
Patent number
US07482342B2

Reaction notes

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