Hydrochloric Acid → HCID 58557357, compound

HRID 1969527Notes

Reaction equation

HRID 1969527 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH:20]=[O:21])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Br[CH2:23][CH:24]=[CH2:25].[In].Cl>C1COCC1.O.CCOC(C)=O>[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH:20]([OH:21])[CH2:25][CH:24]=[CH2:23])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 5359967IndiumHCID 580098835-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde

Product 1

HCID 58557357HCID 58557357, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (5.1 g, 17 mmol) in THF (100 mL) and water (33.3 mL) was added 3-bromoprop-1-ene (2.86 mL, 33.9 mmol) followed by indium (3.89 g, 33.9 mmol). The reaction mixture was stirred for about 15 h at ambient temperature and then aqueous HCl (1 N, 150 mL) and EtOAc (150 mL) were added. The organic layer was separated, dried over anhydrous Na2SO4, filtered, coned in vacuo and purified by chromatography on silica gel eluting with 20-60% EtOAc in heptane to provide 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)but-3-en-1-ol (4 g, 69%) as a thick oil: LC/MS (Table 1, Method a) Rt=2.30 min; MS m/z: 344 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. custompurified by chromatography on silica gel eluting with 20-60% EtOAc in heptane

Sources & evidence

ORD record
ord-4ed06c952d3344f288c06a81cbffa5b3
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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