9-Benzenesulfonyl-3-bromo-5-[1-(2-hydroxyethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile → HCID 67248027, compound

HRID 60331Notes

Reaction equation

HRID 60331 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:29]#[N:30])=[C:18]([O:19][CH:20]4[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][OH:28])[CH2:22][CH2:21]4)[C:13]=3[C:12]3[CH:31]=[C:32](Br)[CH:33]=[N:34][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].ClCCl>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:29]#[N:30])=[C:18]([O:19][CH:20]4[CH2:21][CH2:22][N:23]([CH2:26][CH2:27][OH:28])[CH2:24][CH2:25]4)[C:13]=3[C:12]3[CH:31]=[CH:32][CH:33]=[N:34][C:11]2=3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 672483089-Benzenesulfonyl-3-bromo-5-[1-(2-hydroxyethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Product 1

HCID 67248027HCID 67248027, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 9-benzenesulfonyl-3-bromo-5-[1-(2-hydroxyethyl)-piperidin-4-yloxy]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (283 mg, 0.51 mmol) and palladium on carbon (10 wt %, 50 mg) in industrial methylated spirits (3 mL) and dichloromethane (3 mL) was stirred at ambient temperature under an atmosphere of hydrogen for 48 hours. The reaction vessel was purged with nitrogen then the reaction mixture was filtered through a PTFE filter cup. The filtrate was evaporated in-vacuo and the resultant residue purified by flash chromatography (silica, 24 g column, ISCO, 0-30% methanol in dichloromethane) to afford the title compound as an off-white solid (125 mg, 51%). 1H NMR (300 MHz, CDCl3): 9.59 (s, 1H), 8.76 (dd, J=4.9, 1.7 Hz, 1H), 8.54 (dd, J=7.9, 1.7 Hz, 1H), 8.27-8.26 (m, 2H), 7.62-7.61 (m, 1H), 7.56-7.44 (m, 3H), 5.04-5.03 (m, 1H), 3.70 (t, J=5.2 Hz, 2H), 3.09-3.09 (m, 2H), 2.69 (t, J=5.2 Hz, 2H), 2.51 (t, J=11.0 Hz, 2H), 2.32-2.25 (m, 2H), 2.12-2.10 (m, 2H).

Workup

  1. customThe reaction vessel was purged with nitrogen
  2. filtrationthe reaction mixture was filtered through a PTFE
  3. filtrationfilter cup
  4. customThe filtrate was evaporated in-vacuo
  5. customthe resultant residue purified by flash chromatography (silica, 24 g column, ISCO, 0-30% methanol in dichloromethane)

Sources & evidence

ORD record
ord-14a165dd6cc1440794285c22a1a6b35d
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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