Stannane, tributyl(1-ethoxyethenyl)- → HCID 60142164, compound

HRID 1475937Notes

Reaction equation

HRID 1475937 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:29](/[CH:30]=[CH:31]/[CH2:32][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[C:11]3[CH:12]=[C:13]([C:16]([N:18]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:44]([O:46]CC)=[CH2:45])CCC>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[C:44]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:29](/[CH:30]=[CH:31]/[CH2:32][N:33]3[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)=[C:11]3[CH:12]=[C:13]([C:16]([N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[O:17])[CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1)(=[O:46])[CH3:45]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 60142163HCID 60142163, compound

Product 1

HCID 60142164HCID 60142164, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of Example 41i.e. (E)-2-(4-bromophenyl)-N,N-diisopentyl-3-(3-(piperidin-1-yl)prop-1-en-1-yl)pyrazolo[1,5-a]pyridine-5-carboxamide (553 mg, 0.954 mmol) in toluene (14 mL) was added tributyl(1-ethoxy-vinyl)tin (1.03 g, 2.86 mmol) and tetrakis(triphenylphosphine) palladium (O) (55 mg, 0.05 mmol). The mixture was degassed by bubbling nitrogen into it for 10 minutes and was then heated to 120° C. for 4 h. The mixture was allowed to cool to room temperature and concentrated to a residue and dissolved in THF (12 mL). 1N HCl (3 mL) was added and the mixture was stirred at room temperature for 1 h. Sodium bicarbonate was slowly added until pH was reached 8-9 and the mixture was extracted with ethyl acetate (2×30 mL). The combined organics were washed with brine, filtered and concentrated under reduced pressure.

Workup

  1. customThe mixture was degassed
  2. customby bubbling nitrogen into it for 10 minutes
  3. temperatureto cool to room temperature
  4. concentrationconcentrated to a residue
  5. dissolutiondissolved in THF (12 mL)
  6. addition1N HCl (3 mL) was added
  7. additionSodium bicarbonate was slowly added until pH
  8. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  9. washThe combined organics were washed with brine
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ce67330222541679117d7a596efa3e6
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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