HCID 18466902, compound → HCID 18466914, compound

HRID 2229193Notes

Reaction equation

HRID 2229193 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:4]=1[CH2:10][C:11]1[N:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]2=[N:13][C:12]=1[C:20](OCC)=[O:21].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.CCCCCC>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH2:10][C:11]2[N:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]3=[N:13][C:12]=2[CH2:20][OH:21])[CH:5]=1

Participants

5

Reactant 2

HCID 18466902HCID 18466902, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18466914HCID 18466914, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 3.69 g (9.5 mmol) of ethyl 3-[(2-methoxy-5-bromophenyl)methyl]-imidazolo[1,2-a]pyridine-2-carboxylate in 50 mL tetrahydrofuran is cooled to −78° C. and treated with 25.0 mL (25.0 mmol) of diisobutylaluminum hydride, 1M in hexane. After 1 hr the reaction is allowed to warm up to room temperature and carefully quenched by addition of 25 mL 1M sodium hydroxide. The mixture is extracted with 3×40 mL ethyl acetate and the combined extracts washed with 50 mL brine and dried over anhydrous MgSO4 and the solvent removed in vacuo to afford 3.0 g (91% yield) {3-[(5-bromo-2-methoxyphenyl)methyl]-imidazolo[1,2-a]pyridin-2-yl}methan-1-ol.

Workup

  1. customcarefully quenched by addition of 25 mL 1M sodium hydroxide
  2. extractionThe mixture is extracted with 3×40 mL ethyl acetate
  3. washthe combined extracts washed with 50 mL brine
  4. dry with materialdried over anhydrous MgSO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e22feae06058403ca2c7aa843a1fa213
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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