Hydrochloric Acid → 9-Benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60216Notes

Reaction equation

HRID 60216 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[C:23](Br)[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.C(OCC)(=O)C.Cl>[Pd].C(N(CC)CC)C.CN(C=O)C>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[CH:23][CH:24]=[N:25][C:11]2=3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8857Ethyl AcetateHCID 582664728-(Benzenesulfonyl)-12-bromo-3-hydroxy-5,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2,4,6,10,12-hexaene-4-carbonitrile

Product 1

HCID 582663029-Benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (9.91 g, 23.1 mmol), palladium on carbon hydrogenation catalyst (10 wt %, 1.0 g, 0.94 mmol), ethanol (250 mL), ethyl acetate (50 mL), DMF (50 mL) and triethylamine (50 mL) was stirred at room temperature under an atmosphere of hydrogen for 16 hours. The catalyst was removed by filtration through Celite© and the filtrate evaporated to dryness to give a gum, that was mixed with hydrochloric acid (1M, 100 mL) and sonicated in a laboratory ultrasonic cleaning bath for 30 minutes. The resultant solid was collected by filtration, washed with water then dried under vacuum to afford the title compound as a tan coloured solid (7.19 g, 89%). 1H NMR (400 MHz, DMSO-d6): 9.27 (s, 1H), 8.71 (dd, J=4.9, 1.7 Hz, 1H), 8.68 (dd, J=7.9, 1.7 Hz, 1H), 8.20-8.20 (m, 2H), 7.74-7.73 (m, 1H), 7.60-7.59 (m, 3H).

Workup

  1. customThe catalyst was removed by filtration through Celite©
  2. customthe filtrate evaporated to dryness
  3. customto give a gum, that
  4. customsonicated in a laboratory
  5. customfor 30 minutes
  6. filtrationThe resultant solid was collected by filtration
  7. washwashed with water
  8. customthen dried under vacuum

Sources & evidence

ORD record
ord-64fcaa30da704c2cabb77b0d31134ccd
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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