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Acrylonitrile → 3-(8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)propanenitrile

HRID 1773244
Notes
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Reaction equation

HRID 1773244 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]3[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=3)[C:6]3[CH2:20][CH2:21][NH:22][CH2:23][C:5]=3[C:4]=2[CH:3]=1.[C:24](#[N:27])[CH:25]=[CH2:26].N([O-])=O.[NH4+].C([O-])(O)=O.[Na+]>O>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH2:12][C:13]3[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=3)[C:6]3[CH2:20][CH2:21][N:22]([CH2:26][CH2:25][C:24]#[N:27])[CH2:23][C:5]=3[C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 26004Ammonium nitriteHCID 516892Sodium BicarbonateHCID 578762518-Methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Product 1

HCID 497793773-(8-methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)propanenitrileYield 61.43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8-Methyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (250 mg, 8.19 mmol) was taken into water (3 mL) along with acrylonitrile (0.065 mL, 0.982 mmol) and stirred for 10 min. Ceric ammonium nitrite (133 mg, 0.245 mmol) was added to it at once and the reaction mixture was stirred for 2 h. Product was detected by LCMS and TLC. The reaction mixture was basified with sat. NaHCO3 solution and extracted into EtOAc. The organic layer was dried over anhydrous sodium sulfate, concentrated and the crude product purified by column chromatography (Silica gel, 2-4% MeOH in DCM) to get product 180 mg (61.43%). This was converted into the oxalate salt (143 mg). 1HNMR (CD3OD, Oxalate salt) d (ppm): 7.88 (s, 1H), 7.68-7.64 (d, 1H), 7.38-7.34 (d, 1H), 7.22 (s, 1H), 7.18-7.15 (d, 1H), 7.02-6.97 (d, 1H), 4.42 (s, 2H), 4.40-4.36 (t, 2H), 3.58-3.38 (m, 4H), 3.19-3.08 (m, 4H), 2.88-2.80 (t, 2H), 2.53 (s, 3H), 2.40 (s, 3H).

Workup

  1. stirringwas stirred for 2 h
  2. extractionextracted into EtOAc
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customthe crude product purified by column chromatography (Silica gel, 2-4% MeOH in DCM)

Sources & evidence

ORD record
ord-19ba9c3e6c304442a231ef40359038f4
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09255094B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes