Sodium Carbonate → HCID 57598244, compound

HRID 1497470Notes

Reaction equation

HRID 1497470 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][OH:8])=[N:4][N:3]=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:15]=[CH:14][C:13]([C:2]2[S:6][C:5]([CH2:7][OH:8])=[N:4][N:3]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 633840781,3,4-Thiadiazole-2-Methanol, 5-broMo-

Product 1

HCID 57598244HCID 57598244, compoundYield 65.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (5-bromo-1,3,4-thiadiazol-2-yl)methanol (1.2 g, 6.15 mmol) in toluene (40 ml) and ethanol (40 ml) was added 4-fluorophenyl boronic acid (1.03 g, 7.38 mmol) and 2 M aqueous Na2CO3. The reaction mixture was degassed with argon, Pd(PPh3)4 (0.354 g, 0.355 mmol) was added, the reaction mixture was degassed again with argon for 10 min, and then heated to 100° C. for 2 h. The reaction mixture was evaporated under vacuum to remove ethanol, the reaction mixture was diluted with water (50 mL), and extracted with ethyl acetate (200 mL). The organic extracts were dried over sodium sulphate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was purified by Biotage Isolera® One column (using 30% ethyl acetate and hexane) to give (5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)methanol as a pale yellow solid (0.85 g, 65% yield); LC-MS m/z calcd for [M+H]+ 211.03. found 211.1

Workup

  1. additionwas added
  2. customthe reaction mixture was degassed again 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 (50 mL)
  6. extractionextracted with ethyl acetate (200 mL)
  7. dry with materialThe organic extracts were dried 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 column (using 30% ethyl acetate and hexane)

Sources & evidence

ORD record
ord-b6077b0dca584e63b901f539d10d6337
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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