Diisobutylaluminumhydride → HCID 11639727, compound
Reaction equation
C([O:3][C:4](=O)[CH:5]([C:11]1[N:16]=[C:15]2[S:17][CH:18]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]2=[C:13]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH:12]=1)[C:6](OCC)=[O:7])C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[C:20]1([C:19]2[C:14]3[C:15](=[N:16][C:11]([CH:5]([CH2:6][OH:7])[CH2:4][OH:3])=[CH:12][C:13]=3[NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[S:17][CH:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-{3-Phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-yl}-malonic acid diethyl ester (87 mg, 0.18 mmol) in dry THF (10 ml) was cooled to 0° C. under nitrogen. Diisobutyl Aluminium Hydride (1.46 ml of a 1M solution in hexanes, 1.46 mmol) was added dropwise over 2 min and the mixture stirred at 0° C. for 1 h, then allowed to reach room temperature overnight. The reaction was quenched at 0° C. by adition of 1M Rochelle's salt (10 ml). The mixture was extracted with DCM (3×20 ml), the extracts combined, washed with brine (50 ml), dried over magnesium sulphate and concentrated. The residue was purified on silica, eluting (Ethyl Acetate, 100%) to give 2-{3-Phenyl-4-[(pyridin-2-ylmethyl)-amino]-thieno[2,3-b]pyridin-6-yl}-propane-1,3-diol as a yellow oil. Yield=22.5 mg, (31.4%).
Workup
- waitto reach room temperature overnight
- customThe reaction was quenched at 0° C. by adition of 1M Rochelle's salt (10 ml)
- extractionThe mixture was extracted with DCM (3×20 ml)
- washwashed with brine (50 ml)
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
- customThe residue was purified on silica
- washeluting (Ethyl Acetate, 100%)
Sources & evidence
- ORD record
- ord-1900b554d01f44d2ace325a64ac95959
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193215B2
Reaction notes
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