Potassium Carbonate → 2-(4-Methoxy-phenyl)-thiazole

HRID 1669507

Reaction equation

HRID 1669507 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 112984492-(4-Methoxy-phenyl)-thiazoleYield 50%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-bromothiazole (2.0 g, 12.2 mmol), (4-methoxyphenyl)boronic acid (1.9 g, 12.8 mmol), K2CO3 (5.0 g, 36.5 mmol) and (Ph3P)4Pd (0.7 g, 0.61 mmol) in dioxane (40 mL) was refluxed for 16 h. After the solids were filtered off, the filtrate was concentrated in vacuo. The residue was purified by a column chromatography on silica gel to yield the title compound (1.1 g, 50%). 1HNMR (400 MHz, CDCl3) δ 3.86 (s, 3H), 6.96 (d, J=8.8 Hz, 2H), 7.25 (d, J=3.2 Hz, 1H), 7.81 (d, J=3.2 Hz, 1H), 7.90 (d, J=8.8 Hz, 2H), MS m/z 192 (M+1).

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationAfter the solids were filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-7dcb3fc5b6774c8c97a5eb1a7a548592
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Linked notes

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