HCID 68284104, compound → HCID 68283812, compound

HRID 1469569Notes

Reaction equation

HRID 1469569 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)=[CH:6][N:7]1[C:15]2[CH:14]=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[C:9]2[CH2:17][N:18]([CH3:21])[CH2:19][CH2:20][C:8]1=2>CO.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH:5]([C:22]1[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=1)[CH2:6][N:7]1[C:15]2[CH:14]=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[C:9]2[CH2:17][N:18]([CH3:21])[CH2:19][CH2:20][C:8]1=2

Participants

4

Reactant 1

HCID 68284104HCID 68284104, compound

Product 1

HCID 68283812HCID 68283812, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(2,8-Dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-3-pyridin-4-yl-but-3-enoicacid methyl ester (100 mg, 0.266 mmol) was dissolved in MeOH (10 mL) and 10% dry Pd/C (50 mg) was added and hydrogen gas was purged in to the reaction mixture at RT for 12 h. The reaction was monitored by TLC and LCMS. After consumption of starting material, the reaction mixture was filtered through Celite. The filtrate was concentrated to obtain the crude product, which was recrystallized in ether-hexane to obtained 50 mg of 4-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-3-pyridin-4-yl-butyric acid methyl ester. 1H NMR (CDCl3, freebase) δ (ppm): 8.47 (d, 2H), 7.18 (s, 1H), 7.16 (d, 1H), 6.98 (d, 3H), 4.22 (dd, 1H), 4.05 (dd, 1H), 3.7 (m, 2H), 3.57 (s, 3H), 3.5 (dd, 1H), 2.74 (m, 3H), 2.71 (m, 2H), 2.49 (s, 3H), 2.43 (s, 3H), 2.2 (m, 1H). Separation by chiral HPLC provides enantiomers II-223a-b.

Workup

  1. customhydrogen gas was purged in to the reaction mixture at RT for 12 h
  2. customAfter consumption of starting material
  3. filtrationthe reaction mixture was filtered through Celite
  4. concentrationThe filtrate was concentrated
  5. customto obtain the crude product, which
  6. customwas recrystallized in ether-hexane

Sources & evidence

ORD record
ord-ce790cdf50ca4b2f9d5e7b6b19e1ea0f
Source dataset
uspto-grants-2015_04
Patent number
US09006263B2

Reaction notes

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