Potassium Carbonate → HCID 44548549, compound

HRID 1630727Notes

Reaction equation

HRID 1630727 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17]#[N:18])=[C:15]([SH:19])[N:14]=[C:13]([O:20][CH3:21])[C:12]=2[C:22]#[N:23])=[CH:7][CH:6]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17]#[N:18])=[C:15]([S:19][CH2:29][C:28]3[CH:31]=[CH:32][CH:33]=[C:26]([O:25][CH3:24])[CH:27]=3)[N:14]=[C:13]([O:20][CH3:21])[C:12]=2[C:22]#[N:23])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 40672073-Methoxybenzyl bromideHCID 178494293HCID 178494293, compound

Product 1

HCID 44548549HCID 44548549, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

75 mg (0.229 mmol) of 4-[4-(2-hydroxyethoxy)phenyl]-2-methoxy-6-sulphanylpyridine-3,5-dicarbonitrile together with 36 μl (0.253 mmol) of 3-methoxybenzyl bromide and 52 mg (0.380 mmol) of potassium carbonate are stirred in 1 ml of DMF at room temperature overnight. The reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% formic acid added). This gives 16 mg (56% of theory) of the target compound.

Workup

  1. customThe reaction mixture is purified by preparative HPLC (acetonitrile/water: 10:90→95:5, with 0.1% formic acid added)

Sources & evidence

ORD record
ord-318c143fd378448e8f4a1d043d9eaf23
Source dataset
uspto-grants-2014_07
Patent number
US08791146B2

Reaction notes

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