Water → HCID 58958575, compound

HRID 915584Notes

Reaction equation

HRID 915584 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])[N:7]([CH3:23])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:24]Br.O>C(O)(=O)C>[Br:24][C:9]1[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6][N:7]([CH3:23])[C:8]=1[NH:10][C:11]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 58958588HCID 58958588, compound

Product 1

HCID 58958575HCID 58958575, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-(5-tert-butyl-2-methyl-2H-pyrazol-3-ylamino)-5-methoxy-benzoic acid methyl ester (Example 155, 1.34 g, 4.22 mmol) in acetic acid (27 mL), was added dropwise a solution of Br2 (6.74 g, 4.22 mmol) in acetic acid (5 mL). The reaction was stirred for 5 min, and then water (100 mL) was added. The aqueous phase was extracted with EtOAc, and the combined organic layers were washed with water, and then with NaHCO3 (10% aqueous solution) 10 times. The organic layer was then dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (eluent: 5 to 10% EtOAc in hexane) to give the title compound as a light yellow solid. (1.49 g, 89%). 1H NMR (400 MHz, CDCl3) δ 1.40 (s, 9H), 3.66 (s, 3H), 3.78 (s, 3H), 4.05 (s, 3H), 6.32 (d, 1H), 7.06 (dd, 1H), 7.48 (d, 1H).

Workup

  1. extractionThe aqueous phase was extracted with EtOAc
  2. washthe combined organic layers were washed with water
  3. dry with materialThe organic layer was then dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (eluent: 5 to 10% EtOAc in hexane)

Sources & evidence

ORD record
ord-3aaaebb0400e4397a2cc94da1416c498
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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