(6-Decyloxy-2-fluoropyrid-3-yl)boronic acid → 2-(6-Decyloxy-2-fluoropyrid-3-yl)-5-phenyl-1,3,4-thiadiazole

HRID 1457296Notes

Reaction equation

HRID 1457296 reaction equation
[CH2:1]([O:11][C:12]1[N:17]=[C:16]([F:18])[C:15](B(O)O)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Br[C:23]1[S:24][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:26][N:27]=1>C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1.C(O)C.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>[CH2:1]([O:11][C:12]1[N:17]=[C:16]([F:18])[C:15]([C:23]2[S:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:26][N:27]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 2

HCID 11044681(6-Decyloxy-2-fluoropyrid-3-yl)boronic acidHCID 131041172-Bromo-5-phenyl-1,3,4-thiadiazole

Product 1

HCID 221044332-(6-Decyloxy-2-fluoropyrid-3-yl)-5-phenyl-1,3,4-thiadiazoleYield 82%

Reagents, catalysts & solvents 5

HCID 702EthanolCatalystHCID 962WaterCatalystHCID 1140TolueneCatalystHCID 10340Sodium CarbonateCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

(6-Decyloxy-2-fluoropyrid-3-yl)boronic acid (3.7 g, 12.4 mmol) and 2-bromo-5-phenyl-1,3,4-thiadiazole (1.0 g, 4.15 mmol) are refluxed for 6 hours in a mixture of sodium carbonate (3.95 g), toluene (50 ml), ethanol (25 ml) and water (25 ml) and tetrakis(triphenylphosphine)palladium(0) (5 mol %) as catalyst. Aqueous work-up and column chromatography (SiO2, CH2C12) give 1.4 g (82% of theory) of 2-(6-decyloxy-2-fluoropyrid-3-yl)-5-phenyl-1,3,4-thiadiazole.

Sources & evidence

ORD record
ord-555aab7bbc724e25b0b7fbe83ad81823
Source dataset
uspto-grants-1998_12
Patent number
US05847149

Reaction notes

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