Toluene → HCID 18182508, compound

HRID 1359312Notes

Reaction equation

HRID 1359312 reaction equation
[CH2:1]([C:8]1[C:9]([C:15]#[C:16][C:17]2([OH:25])[CH:22]3[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]3)[CH2:18]2)=[N:10][CH:11]=[C:12](Br)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:26]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27]1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH2:1]([C:8]1[C:9]([C:15]#[C:16][C:17]2([OH:25])[CH:22]3[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]3)[CH2:18]2)=[N:10][CH:11]=[C:12]([C:28]2[CH:29]=[CH:30][S:26][CH:27]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 18182170HCID 18182170, compound

Product 1

HCID 18182508HCID 18182508, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 127 mg of 3-(3-benzyl-5-bromo-2-pyridyl)ethynyl-3-quinuclidinol (Example 22-a), 61.4 mg of 3-thiopheneboronic acid, 55.4 mg of tetrakis (triphenylphosphine)palladium(0), 2 ml of toluene, 0.5 ml of methanol and 1 ml of aqueous 2 mol sodium carbonate solution was stirred at 80° C. for 2 hours in a nitrogen atmosphere. NH-silica gel was added to the reaction solution and the solvent was removed. The residue was subjected to NH-silica gel column chromatography using 3% methanol/ethyl acetate, to give 83.9 mg of the target compound.

Workup

  1. additionNH-silica gel was added to the reaction solution
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-10d88aa629454c1f860195198b86ec9d
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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