HCID 178418361, compound → HCID 11235471, compound

HRID 858025Notes

Reaction equation

HRID 858025 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:31])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][N:8]([CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH:19]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH2:17][CH2:16]1)[C:7]2=[O:30].[N].[H][H]>C(O)C.[Pd]>[Cl:31][C:4]1[CH:5]=[C:6]2[C:11](=[CH:2][CH:3]=1)[N:10]=[CH:9][N:8]([CH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH2:19][CH2:20]1)[C:7]2=[O:30]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178515092HCID 178515092, compound

Product 1

HCID 11235471HCID 11235471, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Catalytic 10% Pd/C was added to a dried hydrogenation bottle under N2 and slowly under nitrogen 8-bromo-6-chloro-3-[3-(4-(1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl)propyl]-4(3H)-quinazolinone (1.52 g, 3.05 mmol) in 150 mL of ethanol was added. This sample was hydrogenated at 30-40 psi hydrogen pressure overnight. The mixture was filtered over celite and concentrated then chromatographed; 6-chloro-3-[3-(4-(1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl)propyl]-4(3H)-quinazolinone was isolated as a yellow powder (0.47 g). Yield 37%; mp 170° C.; MS: 418.8 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ 2.14 (m, 2H), 2.51 (m, 4H), 2.67 (m, 2H), 3.31 (m, 2H), 4.10 (t, J=4.8 Hz), 6.15 (t, 1H), 7.06 (m, 2H), 7.36 (d, 1H), 7.75 (m, 1H), 7.80 (m, 2H), 8.12 (d, 1H), 8.32 (s, 1H), 8.45 (s, 1H), 11.2 (s, 1H).

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered over celite
  3. concentrationconcentrated
  4. customthen chromatographed

Sources & evidence

ORD record
ord-f6a80c8eebfb434c8404cde0c15d36ef
Source dataset
uspto-grants-2006_12
Patent number
US07148235B2

Reaction notes

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