HCID 117778770, compound → HCID 117779032, compound

HRID 1527040Notes

Reaction equation

HRID 1527040 reaction equation
[CH3:1][C:2]1[N:3]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[N:19]3)[C:4]2[C:9]([C:10]=1[C:11]([OH:13])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2>C(O)(=O)C.O=[Pt]=O>[CH3:1][C:2]1[N:3]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][CH2:17][CH2:18][NH:19]3)[C:4]2[C:9]([C:10]=1[C:11]([OH:13])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 117778770HCID 117778770, compound

Product 1

HCID 117779032HCID 117779032, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 2-methyl-1-(quinolin-5-yl)-1H-indole-3-carboxylic acid (Example 40) (25 mg) in acetic acid (3 mL) was added PtO2 (50 mg) at 22° C. The reaction was stirred at 22° C. under H2 ball for 20 hrs. Then the mixture was filtered and the filtrate was purified by column chromatography on silica gel eluted with dichloromethane:methanol=70:1 to the title compound as a yellow solid (20 mg, 71%).

Workup

  1. filtrationThen the mixture was filtered
  2. customthe filtrate was purified by column chromatography on silica gel
  3. washeluted with dichloromethane

Sources & evidence

ORD record
ord-9712bea7e6ac4710b90466c533b9d0a5
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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