Dimethyl Sulfone → 1-(2-(4-(6-Methoxy-2-(5-methylthiophen-2-yl)naphthalen-1-yloxy)phenoxy)ethyl)piperidine

HRID 445229Notes

Reaction equation

HRID 445229 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]=1[O:14][C:15]1[CH:29]=[CH:28][C:18]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:17][CH:16]=1.[CH3:30][C:31]1[S:35][C:34](B(O)O)=[CH:33][CH:32]=1.CS(C)(=O)=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3]([O:14][C:15]1[CH:29]=[CH:28][C:18]([O:19][CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]3)=[CH:17][CH:16]=1)=[C:2]([C:34]1[S:35][C:31]([CH3:30])=[CH:32][CH:33]=1)[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 6213Dimethyl SulfoneHCID 2734374(5-Methylthiophen-2-yl)boronic acidHCID 583385631-(2-(4-(2-Bromo-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidine

Product 1

HCID 583385551-(2-(4-(6-Methoxy-2-(5-methylthiophen-2-yl)naphthalen-1-yloxy)phenoxy)ethyl)piperidine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a 3-necked round bottom flask, add 1-(2-(4-(2-bromo-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidine (25 mg, 75.9 μmol), 5-methylthiophen-2-ylboronic acid (20 mg, 140.86 μmol), tetrakis(triphenylphosphine)palladium (20 mg, 17.3 μmol), and dimethyl sulfone (DMSO) (2 mL). Purge the reaction vessel with nitrogen five times. Heat the mixture was at 100° C. for 6 hours, followed by 80° C. for 40 hours.

Workup

  1. customPurge the reaction vessel with nitrogen five times
  2. temperatureHeat the mixture
  3. waitfollowed by 80° C. for 40 hours

Sources & evidence

ORD record
ord-786571809ffb42dfb69a72ac02d300a0
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

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