HCID 67513601, compound → HCID 57330958, compound

HRID 2172722Notes

Reaction equation

HRID 2172722 reaction equation
Br[C:2]1[C:3]([C:8]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([S:23][CH3:24])[CH:19]=3)[N:14]=2)([OH:12])[CH:9]([CH3:11])[CH3:10])=[N:4][CH:5]=[N:6][CH:7]=1>CCO.[Pd]>[CH3:10][CH:9]([CH3:11])[C:8]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([S:23][CH3:24])[CH:19]=2)[N:14]=1)([C:3]1[CH:2]=[CH:7][N:6]=[CH:5][N:4]=1)[OH:12]

Participants

4

Reactant 1

HCID 67513601HCID 67513601, compound

Product 1

HCID 57330958HCID 57330958, compoundYield 16.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 1-(5-bromopyrimidin-4-yl)-2-methyl-1-(6-(methylthio)quinolin-2-yl)propan-1-ol (H) (90 mg, 0.22 mmol) in EtOH (5 mL) was added 10% Pd/C (40 mg) under inert atmosphere and stirred at RT for 16 h under H2 atmosphere (balloon pressure). After consumption of the starting material (by TLC), the reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 10% EtOAc/hexane to afford 2 (12 mg, 0.036 mmol, 16.6%) as an off-white solid. 1H NMR (500 MHz, CDCl3): δ 9.18 (s, 1H), 8.64 (d, J=5.0 Hz, 1H), 8.10 (d, J=9.0 Hz, 1H), 8.04 (d, J=8.5 Hz, 1H), 7.96-7.94 (m, 2H), 7.59 (dd, J=2.0, 9.0 Hz, 1H), 7.52 (d, J=2.0 Hz, 1H), 6.60 (s, 1H), 3.19-3.16 (m, 1H), 2.58 (s, 3H), 0.84 (d, J=7.0 Hz, 3H), 0.67 (d, J=7.0 Hz, 3H). HPLC: 91.02%. MS (ESI): m/z 326 [M++1].

Workup

  1. customAfter consumption of the starting material (by TLC)
  2. filtrationthe reaction mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-46d5ab5c88244416ad0015526b7eaf30
Source dataset
uspto-grants-2015_06
Patent number
US09056855B2

Reaction notes

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