Methane → HCID 117902800, compound

HRID 1772163Notes

Reaction equation

HRID 1772163 reaction equation
[N:1]([C:4]1[CH:9]=[C:8]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[CH3:19])[CH:12]=[CH:11]2)[CH:7]=[C:6]([N:20]=[N+]=[N-])[N:5]=1)=[N+]=[N-].C.[H][H]>CCOC(C)=O>[CH3:19][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[N:10]([C:8]1[CH:9]=[C:4]([NH2:1])[N:5]=[C:6]([NH2:20])[CH:7]=1)[CH:11]=[CH:12]2

Participants

5

Reactant 3

HCID 297MethaneHCID 117902632HCID 117902632, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 117902800HCID 117902800, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A crude reaction mixture from the preparation of 1-(2,6-diazidopyridin-4-yl)-7-methyl-1H-indole G1 (approx. 340 mg, 1.2 mmol in 2 ml crude mixture) is diluted with EtOAc (10 ml). Under an atmosphere of nitrogen palladium on activated charcoal (10 mg, 10% Pd) is added. At RT the atmosphere is replaced by hydrogen (5 bar) and stirring is continued for 24 h. The mixture is filtered and extracted with an aqueous 0.5 mol/l sodium hydroxide solution. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 120 mg (43%). HPLC-MS: M+H=239; tR=0.81 min (Method—2).

Workup

  1. customA crude reaction mixture
  2. customAt RT
  3. filtrationThe mixture is filtered
  4. extractionextracted with an aqueous 0.5 mol/l sodium hydroxide solution
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-ac01ed4bff0f4f59a1560747c985addf
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

Loading…