Tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylic acid → 9-ethyl-8-iodo-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile
Reaction equation
C([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[C:7]([C:16](O)=[O:17])=[C:6]1[C:19]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[C:24]([I:30])[CH:23]=1)([CH3:21])[CH3:20])(C)(C)C>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(#N)C>[CH2:28]([C:25]1[C:24]([I:30])=[CH:23][C:22]2[C:19]([CH3:21])([CH3:20])[C:6]3[NH:5][C:13]4[C:8]([C:7]=3[C:16](=[O:17])[C:27]=2[CH:26]=1)=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=4)[CH3:29]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylic acid (11 g) was dissolved in Eaton's reagent (200 g) and stirred at room temperature for 30 min. The reaction solution was diluted with acetonitrile (200 ml) and distilled water (400 ml). The precipitated solid was collected by filtration, washed with distilled water, and then dried. The crude product was dissolved in DMA (45 ml), diluted with acetonitrile (20 ml) and distilled water (18 ml), and re-precipitated to obtain the title compound (6.62 g, 70%).
Workup
- distillationdistilled water (400 ml)
- filtrationThe precipitated solid was collected by filtration
- washwashed with distilled water
- customdried
- dissolutionThe crude product was dissolved in DMA (45 ml)
- additiondiluted with acetonitrile (20 ml)
- distillationdistilled water (18 ml)
- customre-precipitated
Sources & evidence
- ORD record
- ord-366818ffdaa84ff88bee1ccb38065f51
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126931B2
Reaction notes
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