Diisobutylaluminum hydride → HCID 67410825, compound
Reaction equation
[F:1][C:2]1([F:30])[CH2:4][CH:3]1[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]3[N:20]=[C:19]([C:21](OCC)=[O:22])[CH:18]=[CH:17][C:16]=3[CH3:26])=[CH:14][C:9]=2[N:8]([CH3:27])[S:7]1(=[O:29])=[O:28].CC(C[AlH]CC(C)C)C>C1COCC1>[F:30][C:2]1([F:1])[CH2:4][CH:3]1[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]3[N:20]=[C:19]([CH2:21][OH:22])[CH:18]=[CH:17][C:16]=3[CH3:26])=[CH:14][C:9]=2[N:8]([CH3:27])[S:7]1(=[O:28])=[O:29]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Ethyl 6-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}-5-methylpyridine-2-carboxylate (26-5) (85 mg, 0.19 mmol, 1 eq) was dissolved in THF (1 mL) and cooled to −78° C. DIBAL-H (0.97 mL, 0.97 mmol, 5.0 eq, 1.0 M in heptane) was added and the mixture was stirred at the same temperature. After 20 minutes the reaction was quenched by an addition of Rochelle's Salt (1 mL) and stirred for 2 hours warming to ambient temperature. The mixture was extracted with EtOAc (10 mL), washed with water (1 mL) and brine (1 mL), dried over MgSO4, filtered and concentrated to afford (6-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}-5-methylpyridin-2-yl)methanol (26-6). HRMS m/z (M+H) 396.1186 found, 396.1188 required.