5-(1-Ethylpiperidin-4-yloxy)-3-isopropenyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile → 5-(1-Ethylpiperidin-4-yloxy)-3-isopropyl-9H-dipyrido[2,3-b:4',3'-d]pyrrole-6-carbonitrile

HRID 1505990Notes

Reaction equation

HRID 1505990 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([O:9][C:10]2[C:15]3[C:16]4[CH:22]=[C:21]([C:23]([CH3:25])=[CH2:24])[CH:20]=[N:19][C:17]=4[NH:18][C:14]=3[CH:13]=[N:12][C:11]=2[C:26]#[N:27])[CH2:5][CH2:4]1)[CH3:2]>[Pd].C(N(CC)CC)C>[CH2:1]([N:3]1[CH2:4][CH2:5][CH:6]([O:9][C:10]2[C:15]3[C:16]4[CH:22]=[C:21]([CH:23]([CH3:24])[CH3:25])[CH:20]=[N:19][C:17]=4[NH:18][C:14]=3[CH:13]=[N:12][C:11]=2[C:26]#[N:27])[CH2:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 1

HCID 582668425-(1-Ethylpiperidin-4-yloxy)-3-isopropenyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Product 1

HCID 582664465-(1-Ethylpiperidin-4-yloxy)-3-isopropyl-9H-dipyrido[2,3-b:4',3'-d]pyrrole-6-carbonitrileYield 27.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A suspension of 5-(1-ethylpiperidin-4-yloxy)-3-isopropenyl-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (98 mg, 0.271 mmol), 10% palladium on carbon (50 mg) and triethylamine (0.5 mL) in IMS (5 mL) was stirred at ambient temperature under a hydrogen atmosphere for 18 h. The mixture was filtered through a PTFE filter and the filtrate concentrated in vacuo to give a brown solid. The resultant solid was purified by flash chromatography (silica, 12 g column, ISCO, 0-5% MeOH in DCM) to afford the title compound as a white solid (27 mg, 27%). 1H NMR (DMSO-Do, 300 MHz): 12.96 (s, 1H), 8.82 (s, 1H), 8.68 (s, 1H), 8.32 (s, 1H), 5.11-4.77 (m, 1H), 3.65-3.48 (m, 2H), 3.28-3.18 (m, 2H), 3.14-2.90 (m, 3H), 2.42-2.18 (m, 4H), 1.37 (d, J=6.9 Hz, 6H), 1.29-1.17 (m, 3H). LCMS (Method H): RT=7.10 min, M+H+=364.

Workup

  1. filtrationThe mixture was filtered through a PTFE
  2. filtrationfilter
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give a brown solid
  5. customThe resultant solid was purified by flash chromatography (silica, 12 g column, ISCO, 0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-fd3990fcdd844c99b044a30a5137af90
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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