1,1'-Carbonyldiimidazole → methyl 4-bromo-2-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}benzoate

HRID 1182239Notes

Reaction equation

HRID 1182239 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([OH:16])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[Br:29][C:30]1[CH:31]=[C:32]([NH2:40])[C:33](=[CH:38][CH:39]=1)[C:34]([O:36][CH3:37])=[O:35].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.O1CCCC1>[Br:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[C:32]([NH:40][C:14](=[O:16])[CH2:13][C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:8][C:7]=2[CH3:12])[CH:31]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 761515-Methoxy-2-methylindole-3-acetic acidHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 17871390Methyl 2-Amino-4-bromobenzoate

Product 1

HCID 69354325methyl 4-bromo-2-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}benzoateYield 66.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Methoxy-2-methyl-3-indole acetic acid (5 g, obtainable from Acros), carbonyidiimidazole (4.44 g) and tetrahydrofuran (120 ml) were stirred at room temperature for 30 min after which methyl 4-bromoanthranilate (5.24 g) and pyridinium tosylate (13.69 g) were added and the mixture refluxed for 14 h. After diluting with dichloromethane (200 ml), the residue was washed with 2M hydrochloric acid (200 ml), 2M sodium hydroxide (200 ml), water (200 ml) and brine (200 ml) and dried (MgSO4). After solidifying by treatment with cyclohexane and ethyl acetate, the solid was triturated with ether to afford methyl 4-bromo-2-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}benzoate (6.54 g), MH+ 433, 435; MH− 431, 433; TR 3.67 min.

Workup

  1. additionwere added
  2. temperaturethe mixture refluxed for 14 h
  3. washthe residue was washed with 2M hydrochloric acid (200 ml), 2M sodium hydroxide (200 ml), water (200 ml) and brine (200 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solid was triturated with ether

Sources & evidence

ORD record
ord-b71ed51311ea431bae8aa2e80406c250
Source dataset
uspto-grants-2007_10
Patent number
US07288564B2

Reaction notes

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