HCID 71285150, compound → HCID 71284398, compound

HRID 1481757Notes

Reaction equation

HRID 1481757 reaction equation
C([O:8][C:9]1[N:17]=[C:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23]([CH3:27])[CH:22]=[C:21]3[C:28]#[N:29])[C:15]([CH2:30][CH3:31])=[C:14]([O:32]CC2C=CC=CC=2)[C:10]=1[C:11]([OH:13])=[O:12])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:28]([C:21]1[C:20]2[C:24](=[CH:25][CH:26]=[C:18]([C:16]3[NH:17][C:9](=[O:8])[C:10]([C:11]([OH:13])=[O:12])=[C:14]([OH:32])[C:15]=3[CH2:30][CH3:31])[CH:19]=2)[N:23]([CH3:27])[CH:22]=1)#[N:29]

Participants

4

Reactant 1

HCID 71285150HCID 71285150, compound

Product 1

HCID 71284398HCID 71284398, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-bis(benzyloxy)-6-(3-cyano-1-methyl-1H-indol-5-yl)-5-ethylnicotinic acid (123 mg, 0.24 mmol) in EtOAc (4 mL) was added Pd/C (10% Degussa type, 30 mg) at room temperature. The flask was evacuated then back-filled with H2 (1 atm) over three cycles. The reaction was monitored by LC-MS. Upon completion, the reaction mixture was filtered through celite then washed with MeOH (ca. 25 mL) thoroughly. The filtrated was concentrated to afford the title compound (58 mg, 72%).

Workup

  1. customThe flask was evacuated
  2. additionthen back-filled with H2 (1 atm) over three cycles
  3. filtrationUpon completion, the reaction mixture was filtered through celite
  4. washthen washed with MeOH (ca. 25 mL) thoroughly
  5. concentrationThe filtrated was concentrated

Sources & evidence

ORD record
ord-76cd503f3f2644dd91c6cb33f6063fa3
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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