Aluminium lithium hydride → HCID 178428426, compound

HRID 218486

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[CH:14]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:24](N(OC)C)=[O:25])[C:13]([C:30]#[N:31])=[C:12]([CH3:32])[NH:11][C:10]=1[CH3:33])#[N:8]>C1COCC1>[CH:24]([C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]([CH:14]3[C:13]([C:30]#[N:31])=[C:12]([CH3:32])[NH:11][C:10]([CH3:33])=[C:9]3[C:7]#[N:8])[CH:16]=2)[NH:20][N:19]=1)=[O:25]

Participants

Conditions

Temperature: 60 °C

Procedure

Lithium aluminum hydride (45 mg, 1.2 mmol) was added portion-wise to a cooled solution of 5-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-N-methoxy-N-methyl-1H-indazole-3-carboxamide (340 mg, 0.94 mmol) in THF (20 mL). After 30 min, the mixture was heated up to 60° C. After 2 hr, the reaction was quenched by the slow addition of ethyl acetate at 5° C. and 0.4 N NaHSO4. The organic layer was washed with brine, dried with Na2SO4, and concentrated. The crude product was purified by column to give 4-(3-formyl-1H-indazol-5-yl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile (200 mg, 70%) (Cpd. No. 145, Table 2). 1H-NMR (400 MHz, DMSO-D6): δ=10.18 (s, 1H), 9.58 (s, 1H), 7.98 (d, 1H), 7.76 (d, 1H), 7.46 (d, 1H), 4.65 (s, 1H), 2.03 (s, 6H) ppm.

Workup

waitAfter 2 hr
customthe reaction was quenched by the slow addition of ethyl acetate at 5° C.
washThe organic layer was washed with brine
dry with materialdried with Na2SO4
concentrationconcentrated
customThe crude product was purified by column

Sources & evidence

ORD record: ord-25fdf6d176984ac792c03a714fd7e2b1
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198456B2

Linked notes

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