8-(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 → 9-Benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 1888524Notes

Reaction equation

HRID 1888524 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>[Pd].C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)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

6

Reactant 1

HCID 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 98%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (5.0 g, 11.7 mmol) and 10% palladium on carbon (500 mg) in industrial methylated spirits (120 mL), ethyl acetate (25 mL), dimethylformamide (25 mL) and triethylamine (25 mL) was stirred at ambient temperature under an atmosphere of hydrogen for 20 h. The reaction vessel was purged with nitrogen then the reaction mixture was filtered through celite. The filtrate was evaporated in vacuo. The resultant brown residue was suspended in aqueous hydrochloric acid (1M, 40 mL) and sonicated for 20 minutes then filtered to afford the title compound as a beige solid (4.0 g, 98%). 1H NMR (DMSO-D6, 300 MHz): 9.27 (d, J=0.8 Hz, 1H), 8.73-8.65 (m, 2H), 8.19 (d, J=7.9 Hz, 2H), 7.78-7.69 (m, 1H), 7.65-7.54 (m, 3H).

Workup

  1. customThe reaction vessel was purged with nitrogen
  2. filtrationthe reaction mixture was filtered through celite
  3. customThe filtrate was evaporated in vacuo
  4. customsonicated for 20 minutes
  5. filtrationthen filtered

Sources & evidence

ORD record
ord-4e4d1ea638ec433298b08740ffd5ee16
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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