tert-Butanol → HCID 58755931, compound

HRID 868742Notes

Reaction equation

HRID 868742 reaction equation
CC(O)(C)C.Br[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)#[CH:15].[N-:23]=[N+:24]=[N-:25].[Na+]>O.[O-]S([O-])(=O)=O.[Cu+2]>[C:19]1([CH3:22])[CH:20]=[CH:21][C:16]([C:14]2[N:23]=[N:24][N:25]([CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[CH:15]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 13018p-EthynyltolueneHCID 33557Sodium AzideHCID 5642092-(Bromomethyl)pyridine

Product 1

HCID 58755931HCID 58755931, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×

Procedure

A mixture of tBuOH (1.5 mL), water (1.5 mL), 2-(bromomethyl)pyridine (253 mg, 1 mmol), 1-ethynyl-4-methylbenzene (122 mg, 1.05 mmol) and NaN3 (68 mg, 1.05 mmol) was added to a microwaveable vial. A cooper wire (50 mg) and CuSO4 (200 μl of 1M aq. solution) was added to the stirred suspension. The vial was sealed and the mixture was irradiated (Microwave, Personal Chemistry, Biotage from Upsala Sweden) at 125° C. for 5 min. The mixture was then diluted with water and the product was extracted to EtOAc, washed with 1M ammonium citrate, 0.25 M aq. HCl and brine, dried over MgSO4, filtered and evaporated. The crude product was purified on silica gel (Eluent: 10% MeOH in DCM) to give 2-((4-p-Tolyl-1H-1,2,3-triazol-1-yl)methyl)pyridine (88 mg, 35%). 1H NMR (300 MHz, dMSO): δ 2.30 (s, 3H), 5.72 (s, 2H), 7.30-7.45 (m, 4H), 7.77-7.89 (m, 3H), 8.60 (s, 1H); MS (M+H, 251).

Workup

  1. additionwas added to a microwaveable vial
  2. customThe vial was sealed
  3. customthe mixture was irradiated (Microwave, Personal Chemistry, Biotage from Upsala Sweden) at 125° C. for 5 min
  4. extractionthe product was extracted to EtOAc
  5. washwashed with 1M ammonium citrate, 0.25 M aq. HCl and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified on silica gel (Eluent: 10% MeOH in DCM)

Sources & evidence

ORD record
ord-9e18f74ef6ce484b9adce689735ed560
Source dataset
uspto-grants-2015_03
Patent number
US08968708B2

Reaction notes

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