Indoline → 4-(2,3-Dihydroindol-1-yl)-6-(4-nitro-phenyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 369707Notes

Reaction equation

HRID 369707 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1>C(O)CCC>[N:20]1([C:2]2[C:3]3[CH:10]=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=4)[NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 10328IndolineHCID 212626054-Chloro-6-(4-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 232824614-(2,3-Dihydroindol-1-yl)-6-(4-nitro-phenyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Under a nitrogen atmosphere, 0.5 g (1.82 mmol) of 4-chloro-6-(4-nitro-phenyl)-7H-pyrrolo-[2,3-d]pyrimidine and 0.43 ml (2.1 equivalents) of 2,3-dihydroindole in 10 ml of abs. n-butanol are heated at reflux for 1.5 hours until the starting material is no longer present in TLC, the desired product precipitating out and being filtered off. The brown crude product is stirred thoroughly in about 20 ml of 1N NaOH for about 15 minutes, and the suspension is filtered with suction and the residue is washed with water, n-butanol and hexane and dried under a high vacuum. 4-(2,3-Dihydroindol-1-yl)-6-(4-nitro-phenyl)-7H-pyrrolo[2,3-d]pyrimidine is obtained in the form of a rust-brown powder having a melting point of>300° C. FAB-MS: (M+H)+ =358 (corresponds to C20H15N5O2); Rf value (toluene-acetone--4:6)=0.40.

Workup

  1. temperatureat reflux for 1.5 hours until the starting material
  2. customthe desired product precipitating out
  3. filtrationbeing filtered off
  4. filtrationthe suspension is filtered with suction
  5. washthe residue is washed with water, n-butanol and hexane
  6. customdried under a high vacuum

Sources & evidence

ORD record
ord-c336f3fe6eaf4a8886d785a78fa60fb1
Source dataset
uspto-grants-2000_10
Patent number
US06140317

Reaction notes

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