Diisobutylaluminumhydride → HCID 90415304, compound

HRID 2271485Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:18][N:19]3[CH:23]=[N:22][C:21]([C:24]#[N:25])=[N:20]3)[CH:11]=[N:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH:5]=[CH:6][CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([CH2:18][N:19]3[CH:23]=[N:22][C:21]([CH2:24][NH2:25])=[N:20]3)[CH:11]=[N:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled solution, −78° C., of 1-((5-(3-chlorophenyl)-6-(difluoromethoxy)pyridin-3-yl)methyl)-1H-1,2,4-triazole-3-carbonitrile (Example 156, 345 mg, 0.95 mmol) in DCM (5 mL) was slowly added diisobutylaluminum hydride (135.64 mg, 0.95 mmol). The mixture was stirred at −78° C. for 1 h. The reaction was quenched with wet sodium sulphate and stirred at room temperature for 30 min. The white aluminum precipitate was filtered and the filtrate concentrated under reduced pressure. Purification (FCC, SiO2, 40-100% EtOAc/DCM, followed by 0-10% MeOH/DCM) afforded the title compound (37 mg, 10%). 1H NMR (400 MHz, CD3OD) δ 8.54 (s, 1H), 8.25 (d, J=2.3 Hz, 1H), 7.92 (d, J=2.3 Hz, 1H), 7.81-7.40 (m, 5H), 5.45 (s, 2H), 3.85-3.82 (m, 2H). [M+H]=366.20.

Workup

customTo a cooled solution, −78° C.
customThe reaction was quenched with wet sodium sulphate
stirringstirred at room temperature for 30 min
filtrationThe white aluminum precipitate was filtered
concentrationthe filtrate concentrated under reduced pressure
customPurification (FCC, SiO2, 40-100% EtOAc/DCM, followed by 0-10% MeOH/DCM)

Sources & evidence

ORD record: ord-0d029acd9ff445afa411b8c735f924ee
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120770B2

Reaction notes

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