Diisobutylaluminum hydride → HCID 54678080, compound

HRID 1244111Notes

Reaction equation

HRID 1244111 reaction equation
CC(C[AlH]CC(C)C)C.[Cl:10][C:11]1[S:23][C:14]2[NH:15][C:16](=[O:22])[C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=2[C:12]=1[C:24]1[CH:33]=[CH:32][C:27]([C:28](OC)=[O:29])=[CH:26][CH:25]=1>C1COCC1>[Cl:10][C:11]1[S:23][C:14]2[NH:15][C:16](=[O:22])[C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=2[C:12]=1[C:24]1[CH:33]=[CH:32][C:27]([CH2:28][OH:29])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 54689838HCID 54689838, compound

Product 1

HCID 54678080HCID 54678080, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1M DIBAL-H (10 mL, 10 mmol) was slowly added to a solution of methyl 4-(2-chloro-5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)benzoate (0.3 g, 0.832 mmol) in anhydrous THF (80 mL) held at −78° C. The solution was then allowed to warm to rt and stirred overnight. The reaction was quenched with MeOH (2 mL) and 1N HCl (5 mL), filtered through silica gel, concentrated and purified on a RP-HPLC system. MS (ESI) m/e 330.9 (M−H)+; 1H NMR (400 MHz, DMSO-d6): δ ppm 7.35 (d, J=8.28, 2H), 7.29 (d, J=7.98, 2H), 4.60 (br s, 1H), 4.55 (s, 2H).

Workup

  1. customheld at −78° C
  2. customThe reaction was quenched with MeOH (2 mL) and 1N HCl (5 mL)
  3. filtrationfiltered through silica gel
  4. concentrationconcentrated
  5. custompurified on a RP-HPLC system

Sources & evidence

ORD record
ord-1aee46bb79cf483f91693a04052f27e7
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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