2-(Tributylstannyl)pyridine → HCID 11662465, compound

HRID 2111828Notes

Reaction equation

HRID 2111828 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][CH:14]=1)[C:5]2=[O:29].C([Sn](CCCC)(CCCC)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)CCC>C1(C)C=CC=CC=1>[CH3:12][C:7]1[N:6]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:15][CH:14]=2)[C:5](=[O:29])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[CH:3]=2)[N:8]=1

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 11532621HCID 11532621, compound

Product 1

HCID 11662465HCID 11662465, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

6-bromo-2-methyl-3-{4-[3-(1-piperidinyl)propoxy]phenyl}-4(3H)-quinazolinone synthesized in Example 34 (100 mg, 0.25 mmol) and 2-(tributylstannyl)pyridine (90 mg, 0.25 mmol) were dissolved in toluene (1 mL), and the atmosphere in the system was replaced by nitrogen. Palladium tetrakis(triphenylphosphine) complex (30 mg, 0.025 mmol) was added, and stirred at 120° C. for 12 hours. Insoluble matter was filtered off through cerite, chloroform was added to the filtrate, the organic phase was washed with distilled water, and dried with anhydrous sodium sulfate. The product was purified by silica gel column chromatography (chloroform/methanol=9/1), and the target substance (20 mg, 20%) was obtained as a colorless solid.

Workup

  1. additionPalladium tetrakis(triphenylphosphine) complex (30 mg, 0.025 mmol) was added
  2. filtrationInsoluble matter was filtered off through cerite, chloroform
  3. additionwas added to the filtrate
  4. washthe organic phase was washed with distilled water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe product was purified by silica gel column chromatography (chloroform/methanol=9/1)
  7. customthe target substance (20 mg, 20%) was obtained as a colorless solid

Sources & evidence

ORD record
ord-a1b557c5e3bd4ebab888625632fc873e
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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