Sodium Carbonate → HCID 22350273, compound

HRID 896471Notes

Reaction equation

HRID 896471 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[S:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:12]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O>COCCOC.CCOC(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>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:8]1[S:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343542-Fluorophenylboronic acidHCID 3614103Ethyl 2-bromothiazole-5-carboxylate

Product 1

HCID 22350273HCID 22350273, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0) (0.58 g, 0.5 mmol), and a degassed solution of 2.0M Na2CO3 (10 mL) are added to a degassed solution of ethyl 2-bromo-1,3-thiazole-5-carboxylate (1.18 g, 5.0 mmol) and 2-fluorophenylboronic acid (0.77 g, 5.5 mmol) in DME (10 mL). The resulting suspension is stirred under argon at 80° C. for 4 hr. The reaction mixture is cooled, diluted with EtOAc, and then washed with two portions of 1.0 M NaOH, then one portion of brine. The combined organic phases are concentrated in vacuo, and the resulting oil purified with flash chromatography to give ethyl 2-(2-fluorophenyl)-1,3-thiazole-5-carboxylate. Yield 37%. HRMS (FAB) calculated for C12H10FNO2S+H 252.0495, found 252.0496.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washwashed with two portions of 1.0 M NaOH
  3. concentrationThe combined organic phases are concentrated in vacuo
  4. customthe resulting oil purified with flash chromatography

Sources & evidence

ORD record
ord-01bdeba38a724e9096e6e77e78c3a31f
Source dataset
uspto-grants-2005_07
Patent number
US06919359B2

Reaction notes

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