Hydrochloric Acid → [6-(5-Methyl-[1,2,4]oxadiazol-3-yl)-naphthalen-2-yl]-boronic acid

HRID 1697266Notes

Reaction equation

HRID 1697266 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:17]1[N:21]=[C:20]([CH3:22])[O:19][N:18]=1)[CH:11]=[CH:10]2.C[O:24][B:25](OC)[O:26]C.Cl>O1CCCC1>[CH3:22][C:20]1[O:19][N:18]=[C:17]([C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([B:25]([OH:26])[OH:24])[CH:16]=[CH:15]3)[N:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 595340753-(6-Bromo-naphthalen-2-yl)-5-methyl-[1,2,4]oxadiazoleHCID 178418339Butyllithium

Product 1

HCID 59534019[6-(5-Methyl-[1,2,4]oxadiazol-3-yl)-naphthalen-2-yl]-boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4.76 ml n-butyllithium solution (1.6 M in hexane) are added dropwise to 1.00 g 3-(6-bromo-naphthalen-2-yl)-5-methyl-[1,2,4]oxadiazole in 15 ml of tetrahydrofuran at −78° C. The reaction mixture is stirred for another hour at −78° C., then 1.94 ml trimethylborate are added dropwise. Then the reaction mixture is left to heat up to ambient temperature and stirred overnight at this temperature. Then 9 ml 1 N hydrochloric acid are added while cooling with an ice bath. After 10 minutes at ambient temperature the tetrahydrofuran is distilled off in vacuo using the rotary evaporator and the flask residue is extracted with ethyl acetate. The combined organic extracts are dried on magnesium sulphate and evaporated down. The crude product is stirred with diisopropylether, suction filtered and dried.

Workup

  1. waitThen the reaction mixture is left
  2. temperatureto heat up to ambient temperature
  3. stirringstirred overnight at this temperature
  4. temperaturewhile cooling with an ice bath
  5. distillationAfter 10 minutes at ambient temperature the tetrahydrofuran is distilled off in vacuo
  6. customthe rotary evaporator
  7. extractionthe flask residue is extracted with ethyl acetate
  8. customThe combined organic extracts are dried on magnesium sulphate
  9. customevaporated down
  10. stirringThe crude product is stirred with diisopropylether, suction
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-345e37d6692c4f4db879efe903993476
Source dataset
uspto-grants-2012_04
Patent number
US08163911B2

Reaction notes

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