Hydrochloric Acid → HCID 71742675, compound

HRID 1503357Notes

Reaction equation

HRID 1503357 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-a06f4f1a69a44fb495e22a38589333d9
Source dataset
uspto-grants-2015_12
Patent number
US09212184B2

Reaction notes

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