HCID 53236843, compound → HCID 53236844, compound

HRID 469517Notes

Reaction equation

HRID 469517 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[N:10]([NH:19][C:20](=[O:29])[CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[N:9]=2)=[CH:4][CH:3]=1>CO.[Pd]>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:20]([NH:19][N:10]2[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:18])=[O:29])=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 53236843HCID 53236843, compound

Product 1

HCID 53236844HCID 53236844, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of the product of Example 3 (29.9 mg, 0.064 mmol) and 10% Pd/C (catalytic amount) in MeOH (1 mL) was stirred under H2 (1 atm) overnight, filtered though Celite, and concentrated to give the title compound (24.9 mg, 0.064 mmol) as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 11.70 (s, 1H), 8.45-8.35 (m, 1H), 8.01-7.90 (m, 2H), 7.76-7.68 (m, 1H), 7.58 (s, 5H), 7.40 (s, 4H), 3.70 (s, 2H); MS (ESI−) M/Z 388 (M−H)−.

Workup

  1. filtrationfiltered though Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a4b85e0127824896afc94e2c721aeef3
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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