Toluene → HCID 58611967, compound

HRID 751265Notes

Reaction equation

HRID 751265 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(O[C:21](=[O:33])[CH2:22][C:23]1[N:27]2[CH:28]=[C:29]([Br:32])[CH:30]=[CH:31][C:26]2=[N:25][CH:24]=1)C.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C1COCC1.CO>[Br:32][C:29]1[CH:30]=[CH:31][C:26]2[N:27]([C:23]([CH2:22][C:21]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[O:33])=[CH:24][N:25]=2)[CH:28]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8083MorpholineHCID 21225700DiisobutylaluminumhydrideHCID 46839968Ethyl (6-bromoimidazo[1,2-a]pyridin-3-yl)acetate

Product 1

HCID 58611967HCID 58611967, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 0.5M diisobutylaluminum hydride in toluene (4.6 mL, 2.29 mmol) to a solution of (6-bromo-imidazo[1,2-a]pyridin-3-yl)-acetic acid ethyl ester (0.65 g, 2.29 mmol) and morpholine (5 mL) in THF (40 mL) at −78° C. Gently warm the reaction to room temperature and dilute carefully with methanol. Filter and concentrate the filtrate. Flash chromatography gives the subtitled compound (0.24 g, 32%) as a white solid. MS ES+ m/e 324.0, 326.0 (M+1).

Workup

  1. temperatureGently warm
  2. customthe reaction to room temperature
  3. filtrationFilter
  4. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-5eb284f7f6f34e51a019530a87c698a0
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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