Sodium borohydride → 5-[2-Cyano-6-ethoxy-5-(1-hydroxyethyl)-3-methylphenyl]-N,N-dimethylpyridine-2-carboxamide

HRID 1499904Notes

Reaction equation

[BH4-].[Na+].[C:3]([C:6]1[C:7]([O:26][CH2:27][CH3:28])=[C:8]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])=[N:19][CH:20]=2)[C:9]([C:13]#[N:14])=[C:10]([CH3:12])[CH:11]=1)(=[O:5])[CH3:4]>CO>[C:13]([C:9]1[C:10]([CH3:12])=[CH:11][C:6]([CH:3]([OH:5])[CH3:4])=[C:7]([O:26][CH2:27][CH3:28])[C:8]=1[C:15]1[CH:16]=[CH:17][C:18]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])=[N:19][CH:20]=1)#[N:14]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium tetrahydroborate (370 mg, 9.8 mmol) was added to a mixture of 5-(3-acetyl-6-cyano-2-ethoxy-5-methylphenyl)-N,N-dimethylpyridine-2-carboxamide (2.3 g, 6.5 mmol) in methanol (100 mL) at 0° C. The reaction was stirred at 0° C. for 1 h. The reaction was partitioned between water and EtOAc. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give the crude product 5-[2-cyano-6-ethoxy-5-(1-hydroxyethyl)-3-methylphenyl]-N,N-dimethylpyridine-2-carboxamide as a clear oil (13 g, 99%). LCMS calculated for C20H24N3O3(M+H)+: m/z=354.1; found: 354.2.

Workup

customThe reaction was partitioned between water and EtOAc
washThe combined organic layer was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-4882e27bcdcc4bd29f58af4dbe3ee4bd
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199982B2

Reaction notes

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