Sodium Carbonate → 2-(3-Fluorophenyl)-1,3-thiazole-5-carbaldehyde

HRID 1497422Notes

Reaction equation

HRID 1497422 reaction equation
Br[C:2]1[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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:9][C:10]1[CH:11]=[C:12]([C:2]2[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=2)[CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 27732592-Bromo-1,3-thiazole-5-carbaldehyde

Product 1

HCID 450368252-(3-Fluorophenyl)-1,3-thiazole-5-carbaldehydeYield 54%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-bromothiazole-5-carbaldehyde (0.6 g, 3.125 mmol) in toluene (2 mL) and ethanol (1 mL) was added 4-fluorophenyl boronic acid (0.524 g, 3.75 mmol), 2 M solution of aq. Na2CO3. The reaction mixture degassed with argon, tetrakis (0.180 g, 0.156 mmol) was added, the reaction mixture was again degassed with argon for 10 min, and heated to 120° C. for 4 h. The reaction mixture was evaporated under vacuum to remove ethanol, the reaction mixture was diluted with water (10 mL), extracted with ethyl acetate (50 mL) and dried over sodium sulphate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was purified by Biotage Isolera® One chromatography (using 6% ethyl acetate and hexane) to give 2-(3-fluorophenyl)thiazole-5-carbaldehyde (0.350 g, 54% yield); 1H NMR (400 MHz, DMSO-d6): δ 8.78 (s, 1H), 7.90 (dd, 2H), 7.61 (q, 1H); 7.44 (t, 1H); LC-MS m/z calcd for [M+H]+ 208.02. found 208.0.

Workup

  1. additionwas added
  2. customthe reaction mixture was again degassed with argon for 10 min
  3. customThe reaction mixture was evaporated under vacuum
  4. customto remove ethanol
  5. additionthe reaction mixture was diluted with water (10 mL)
  6. extractionextracted with ethyl acetate (50 mL)
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto obtain crude product
  11. customThe crude product was purified by Biotage Isolera® One chromatography (using 6% ethyl acetate and hexane)

Sources & evidence

ORD record
ord-3f5972b6288f49cc9c9a06d141f17dab
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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