Triacetoxyperiodinane → HCID 57955298, compound

HRID 73670Notes

Reaction equation

HRID 73670 reaction equation
[CH2:1]([C:3]([C:6]1[C:7]([Br:23])=[C:8]2[N:13]([C:14]=1[CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[N:12]=[CH:11][N:10]=[C:9]2[NH2:22])([OH:5])C)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1>[NH2:22][C:9]1[C:8]2=[C:7]([Br:23])[C:6]([C:3](=[O:5])[CH3:1])=[C:14]([CH2:15][N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[N:13]2[N:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66640996Ethyl 1-[4-amino-5-bromo-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]ethanol

Product 1

HCID 57955298HCID 57955298, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of THF (100 mL) was added ethyl 1-[4-amino-5-bromo-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]ethanol (419 mg, 1.18 mmol) followed by Dess-Martin periodinane (748 mg, 1.76 mmol). The solution was stirred at rt for 1 h and then quenched by addition of aqueous saturated sodium thiosulfate and NaHCO3 (100 mL) followed by EtOAc (100 mL) to the reaction. The solution was stirred for 30 min at rt and then transferred to a separatory funnel. The organic layer was isolated while the aqueous layers were back extracted with EtOAc (2×50 mL). The combined organic layers were collected, dried (MgSO4), filtered, and concentrated to dryness. The crude material was then triturated with THF-Et2O. The solid was collected, washed with Et2O (150 mL), and dried under vacuum. The mother liquor was concentrated and purified by MPLC (Isco) 100% CH2Cl2 to 9:1 v/v CH2Cl2-MeOH. The resulting purified fractions were combined with the solid and concentrated in vacuo yielding 344 mg of the above compound (0.97 mmol, yield 83%). 1H-NMR (DMSO-d6) δ 8.35 (br s, 1H), 7.94 (s, 1H), 7.13 (br s, 1H), 4.02 (s, 2H), 3.47 (m, 4H), 2.64 (s, 3H), 2.35 (m, 4H); MS [M+H]+=354.0; LCMS RT=1.11 min.

Workup

  1. customquenched by addition of aqueous saturated sodium thiosulfate and NaHCO3 (100 mL)
  2. customfollowed by EtOAc (100 mL) to the reaction
  3. stirringThe solution was stirred for 30 min at rt
  4. customtransferred to a separatory funnel
  5. customThe organic layer was isolated while the aqueous layers
  6. extractionwere back extracted with EtOAc (2×50 mL)
  7. customThe combined organic layers were collected
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customThe crude material was then triturated with THF-Et2O
  12. customThe solid was collected
  13. washwashed with Et2O (150 mL)
  14. customdried under vacuum
  15. concentrationThe mother liquor was concentrated
  16. custompurified by MPLC (Isco) 100% CH2Cl2 to 9:1 v/v CH2Cl2-MeOH
  17. customThe resulting purified fractions
  18. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd97e996734148b79aed13f4a1fa78b5
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

Loading…