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

HRID 907194Notes

Reaction equation

HRID 907194 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) was heated to reflux overnight. The solution was cooled and evaporated, and the residue taken up in ethyl acetate (50 mL). This was washed with water and saturated brine (50 mL each), then dried over anhydrous sodium sulfate, filtered and evaporated. The resulting solid was 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 was cooled
  3. customevaporated
  4. washThis was 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 was triturated with ether
  9. filtrationcollected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-031ad0a84c3e41658887120aedb5aba3
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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