Diisobutylaluminum hydride → HCID 67410825, compound

HRID 515229Notes

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

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.

Workup

customAfter 20 minutes the reaction was quenched by an addition of Rochelle's Salt (1 mL)
stirringstirred for 2 hours
temperaturewarming to ambient temperature
extractionThe mixture was extracted with EtOAc (10 mL)
washwashed with water (1 mL) and brine (1 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-6cb11a4d9f084cf89e15373ca877446a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108937B2

Reaction notes

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