Diisobutylaluminumhydride → HCID 59682036, compound

HRID 1394653Notes

Reaction equation

HRID 1394653 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([C:24]3[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[CH:27]=[C:26]([CH:33]([CH3:35])[CH3:34])[C:25]=3[O:36][CH2:37][CH3:38])=[CH:22][N:23]=2)[CH:20]=1)=O>ClCCl>[CH2:37]([O:36][C:25]1[C:26]([CH:33]([CH3:34])[CH3:35])=[CH:27][C:28]([CH:30]([CH3:32])[CH3:31])=[CH:29][C:24]=1[C:21]1[N:19]2[CH:20]=[C:15]([CH2:13][OH:12])[CH:16]=[CH:17][C:18]2=[N:23][CH:22]=1)[CH3:38]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 59682038HCID 59682038, compound

Product 1

HCID 59682036HCID 59682036, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Diisobutylaluminum hydride (2.4 ml, 1M soln., 2.4 mmol) was added dropwise to a solution of 3-(2-ethoxy-3,5-diisopropyl-phenyl)-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (300 mg, 0.79 mmol) in dichloromethane (10 mL) which had been cooled to −78° C. under a nitrogen atmosphere. After the addition was complete, the reaction was kept at −78° C. for 4 h, then quenched with with methanol (10 mL). After addition of the methanol, the mixture was poured into water, filtered and the solution evaporated to a residue. The residue was purified by silica gel chromatography (2.5% MeOH in dichloromethane) to give [3-(2-ethoxy-3,5-diisopropyl-phenyl)-imidazo[1,2-a]pyridin-6-yl]-methanol as a clear glass (102 mg, 38%). 1H NMR (250 MHz, CDCl3): δ 8.01 (s, 1H), 7.70 (bs, 1H), 7.64 (d, 1H, J=9.4), 7.24 (m, 2H), 7.12 (d, 1H, J=0.62), 4.73 (s, 1H), 3.45 (m, 1H), 3.35 (q, 2H, J=7.0), 1.34 (s, 3H), 1.31 (s, 3H), 1.30 (s, 3H), 1.29 (s, 3H), 0.84 (t, 3H, J=7.0), MS [EI+] 353 (M+H)+.

Workup

  1. additionAfter the addition
  2. customquenched with with methanol (10 mL)
  3. additionAfter addition of the methanol
  4. additionthe mixture was poured into water
  5. filtrationfiltered
  6. customthe solution evaporated to a residue
  7. customThe residue was purified by silica gel chromatography (2.5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-f0fab459e995413c8d3f8a628a227e25
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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