Hydrochloric Acid → HCID 71742675, compound

HRID 925586Notes

Reaction equation

HRID 925586 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([Br:16])[C:5]2[N:6]([CH:8]=[C:9]([C:11](OCC)=[O:12])[N:10]=2)[CH:7]=1.CC(C[AlH]CC(C)C)C.Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[N:3]=[C:4]([Br:16])[C:5]2[N:6]([CH:8]=[C:9]([CH2:11][OH:12])[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 19827087Ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate

Product 1

HCID 71742675HCID 71742675, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate (13.95 g, 40 mmol) in toluene (558 mL) at 0° C. was added 80 mL DIBAH (120 mmol, 3 eq, 1.5M in toluene) dropwise. After stirring overnight at rt, the solution was poured on 1M HCl, extracted with ethyl acetate and the organic phase was washed with water, sole, dried over sodium sulphate and filtered. Removal of the solvent and recrystallyzation from DCM yielded 5.55 g (45.2%) (6,8-dibromoimidazo[1,2-a]pyrazin-2-yl)methanol: 1H-NMR (300 MHz, d6-DMSO): δ=8.93 (s, 1H), 8.05 (s, 1H), 5.46 (bs, 1H), 4.63 (s, 2H) ppm. UPLC-MS: RT=0.73 min; m/z 308.0 [MH+]; required MW=307.0.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic phase was washed with water
  3. dry with materialsole, dried over sodium sulphate
  4. filtrationfiltered
  5. customRemoval of the solvent and recrystallyzation from DCM

Sources & evidence

ORD record
ord-aba7c4ce430445db8056e46455d672a7
Source dataset
uspto-grants-2016_03
Patent number
US09284317B2

Reaction notes

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