Nitrogen → HCID 10736491, compound

HRID 1600842Notes

Reaction equation

HRID 1600842 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:21])[CH2:11][C:12]#[C:13][Si](CC)(CC)CC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:23]1[CH:29]=[C:28]([N:30]2[CH:34]=[N:33][N:32]=[CH:31]2)[CH:27]=[CH:26][C:24]=1[NH2:25].[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N#N>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][CH2:9][C@H:10]([OH:21])[CH2:11][C:12]1[C:23]2[C:24](=[CH:26][CH:27]=[C:28]([N:30]3[CH:34]=[N:33][N:32]=[CH:31]3)[CH:29]=2)[NH:25][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 10517287HCID 10517287, compoundHCID 10685967HCID 10685967, compound

Product 1

HCID 10736491HCID 10736491, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

This acetylene (7.6 g, 25 mmol), 2-iodo-4-(1,2,4-triazol-4-yl)aniline (5.6 g, 19.6 mmol), LiCl (927 mg, 19.7 mmol), Na2CO3 (8.37 g, 79 mmol), and Ph3P (1.03 g, 3.93 mmol) were stirred in DMF (200 ml) at r.t. for 2 h whilst N2 gas was bubbled through the mixture. Pd(OAc)2 (441 mg, 1.97 mmol) was then added, and the reaction heated at 100° C. for 20 h. The mixture was cooled, filtered and evaporated. H2O (500 ml) was added, and extracted with ethyl acetate (×5). The combined organic layers were washed with H2O, brine, dried, and evaporated. A mixture of EtOH and 5M HCl (300 ml, 1:1 v/v) was added, and the solution stood at r.t. for 18 h, then poured into saturated K2CO3, and extracted with EtOAc (×3). The organic layers were washed with water and brine, dried, evaporated, and purified by flash chromatography, eluting with CH2Cl2 :MeOH (92:8 v/v) to give (R)-3-(3-benzyloxy-2-hydroxyprop-1-yl)-5-(1,2,4-triazol-4-yl)indole (1.81 g, 26%).

Workup

  1. customwas bubbled through the mixture
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customevaporated
  5. additionH2O (500 ml) was added
  6. extractionextracted with ethyl acetate (×5)
  7. washThe combined organic layers were washed with H2O, brine
  8. customdried
  9. customevaporated
  10. additionA mixture of EtOH and 5M HCl (300 ml, 1:1 v/v)
  11. additionwas added
  12. additionpoured into saturated K2CO3
  13. extractionextracted with EtOAc (×3)
  14. washThe organic layers were washed with water and brine
  15. customdried
  16. customevaporated
  17. custompurified by flash chromatography
  18. washeluting with CH2Cl2 :MeOH (92:8 v/v)

Sources & evidence

ORD record
ord-f6d51e8f0fc2492fabeea76c8ce975b2
Source dataset
uspto-grants-1999_11
Patent number
US05977116

Reaction notes

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