HCID 59425459, compound → HCID 59425699, compound

HRID 907170Notes

Reaction equation

HRID 907170 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([N+:23]([O-])=O)[CH:17]=1)[CH3:2]>[Pd].CCOC(C)=O>[NH2:23][C:18]1[CH:17]=[C:16]([C:4]2[N:3]([CH2:1][CH3:2])[C:11]3[C:6]([C:5]=2[C:14]#[N:15])=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=3)[CH:21]=[CH:20][C:19]=1[OH:22]

Participants

4

Reactant 1

HCID 59425459HCID 59425459, compound

Product 1

HCID 59425699HCID 59425699, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-Ethyl-2-(4-hydroxy-3-nitrophenyl)-6-methoxy-1H-indole-3-carbonitrile (369 mg, 1.1 mmol), prepared as in example 1Gd, was combined with EtOAc (20 mL) and Pd/C (150 mg, 10%). This mixture was hydrogenated at 30 p.s.i. for 1 h. This was filtered through celite. The filtrate was concentrated and triturated with ether to yield 2-(3-amino-4-hydroxyphenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (307 mg, 91%), compound 322, as a white solid.

Workup

  1. filtrationThis was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. customtriturated with ether

Sources & evidence

ORD record
ord-bfabb754e99b442caf3de1de27e5cf61
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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