4-Chloro-2-phenylquinazoline → 1-ethyl-6-methoxy-2-[4-(2-phenylquinazolin-4-ylamino)-phenyl]-1H-indole-3-carbonitrile

HRID 506097Notes

Reaction equation

HRID 506097 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:4][CH:3]=1.Cl[C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:25]=1.C(N(C(C)C)CC)(C)C>C(O)C>[CH2:21]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=2)[C:16]([C:17]#[N:18])=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=[C:26]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:25]=2)=[CH:7][CH:6]=1)[CH3:22]

Participants

5

Reactant 3

HCID 809774-Chloro-2-phenylquinazolineHCID 81531DiisopropylethylamineHCID 116017362-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile

Product 1

HCID 594264591-ethyl-6-methoxy-2-[4-(2-phenylquinazolin-4-ylamino)-phenyl]-1H-indole-3-carbonitrileYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (100 mg, 0.343 mmol), 4-chloro-2-phenyl-quinazoline (83 mg, 0.34 mmol) and diisopropylethylamine (0.10 mL, 0.57 mmol) in absolute ethanol (3 mL) is heated to reflux overnight. The solution is cooled and evaporated, and the residue taken up in ethyl acetate (50 mL). This is washed with water and saturated brine (50 mL each), then dried over anhydrous sodium sulfate, filtered and evaporated. The resulting solid is triturated with ether, collected by filtration and dried under vacuum to afford 1-ethyl-6-methoxy-2-[4-(2-phenylquinazolin-4-ylamino)-phenyl]-1H-indole-3-carbonitrile (139 mg, 0.280 mmol, 82%).

Workup

  1. temperatureto reflux overnight
  2. temperatureThe solution is cooled
  3. customevaporated
  4. washThis is washed with water and saturated brine (50 mL each)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid is triturated with ether
  9. filtrationcollected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-bbcb3a2d826b4b8a840213dde9026db6
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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