Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-[2-(5-Bromo-1H-indol-3-yl)ethyl]-3-{3-[(propan-2-yl)oxy]phenyl}quinazolin-4(3H)-one

HRID 1461362Notes

Reaction equation

HRID 1461362 reaction equation
CC1(C)O[C:6](=O)[CH:5]([CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Br:19])[CH:17]=3)[NH:12][CH:11]=2)C(=O)O1.[NH2:22][C:23]1[CH:41]=[CH:40][CH:39]=[CH:38][C:24]=1[C:25]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH:35]([CH3:37])[CH3:36])[CH:29]=1)=[O:26].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>N1C=CC=CC=1>[Br:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:9][CH2:5][C:6]1[N:27]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH:35]([CH3:36])[CH3:37])[CH:29]=2)[C:25](=[O:26])[C:24]2[C:23](=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:22]=1

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 148430222-Amino-N-{3-[(propan-2-yl)oxy]phenyl}benzamideHCID 15881114HCID 15881114, compound

Product 1

HCID 43554502-[2-(5-Bromo-1H-indol-3-yl)ethyl]-3-{3-[(propan-2-yl)oxy]phenyl}quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-yl)methyl-5-bromoindole (4.12 g, 12 mmol), 2-amino-N-(3-isopropoxyphenyl)benzamide (3.48 g, 13 mmol), and PPTS (1.64 g, 6.5 mmol) in 50 ml of pyridine was refluxed for 3.5 days. The reaction mixture was then evaporated in vacuo to dryness, and the residue was taken up in methylene chloride. The product was chromatographed (30% ethyl acetate/hexanes, SiO2) and the title product (2.13 g, 36%) crystallized by allowing the fractions containing product to evaporate: mp 179°-181° C.

Workup

  1. customThe reaction mixture was then evaporated in vacuo to dryness
  2. customThe product was chromatographed (30% ethyl acetate/hexanes, SiO2)
  3. customthe title product (2.13 g, 36%) crystallized
  4. additioncontaining product
  5. customto evaporate

Sources & evidence

ORD record
ord-d9490aa01b734ad4b0382c5593939346
Source dataset
uspto-grants-1991_12
Patent number
US05075313

Reaction notes

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