Acetic Acid → 2-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1 H-indol-3-yl) benzoic acid

HRID 1684003Notes

Reaction equation

HRID 1684003 reaction equation
Cl.[Br:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)N)=[CH:5][CH:4]=1.O=[C:21]([CH3:32])[CH2:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25]([OH:27])=[O:26].C(O)(=O)C>C1(C)C=CC=CC=1>[Br:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:10]3[C:15](=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[C:22]([C:23]3[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=3[C:25]([OH:27])=[O:26])=[C:21]2[CH3:32])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 110739652-(2-oxopropyl)benzoic AcidHCID 19041688N-(p-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine hydrochloride

Product 1

HCID 538358182-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1 H-indol-3-yl) benzoic acidYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

A solution of the hydrazine from Example 1, Step 5, (675 mg, 2.2 mmol), 2-(2-oxopropyl)benzoic acid (425 mg, 2.4 mmol) and acetic acid (314 μL, 5.5 mmol) in toluene was warmed to 65° C. for 1-- h after what the mixture was evaporated and acetic acid was removed with the help of heptane in vacuo. To a portion of the residue (100 mg) in dioxane (1 mL) was added 4M HCl in dioxane (2 mL) and the mixture was heated to 65° C. for 1 h. It was then cooled to 25° C. and poured on a mixture of ice water and ethyl acetate. The organic layer was washed with brine and dried with MgSO4. Removal of the solvents yielded a residue which was purified by flash chromatography. The remaining portion of the intermediate was processed identically and combined to give the product (357 mg). Anal. Calcd. for C24H20BrNO3 : C, 64.01; H, 4.48; N, 3.11. Found: C, 63.92; H, 4.51; N, 3.04.

Workup

  1. customwas evaporated
  2. customacetic acid was removed with the help of heptane in vacuo
  3. additionTo a portion of the residue (100 mg) in dioxane (1 mL) was added 4M HCl in dioxane (2 mL)
  4. temperatureIt was then cooled to 25° C.
  5. additionpoured on a mixture of ice water and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried with MgSO4
  8. customRemoval of the solvents
  9. customyielded a residue which
  10. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-98aaf0b99451492bbfad886915b060e9
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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