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

HRID 1499904ノート

反応式

HRID 1499904 の反応式
[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]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 866778265-(3-acetyl-6-cyano-2-ethoxy-5-methylphenyl)-N,N-dimethylpyridine-2-carboxamide

生成物 1

HCID 866778275-[2-Cyano-6-ethoxy-5-(1-hydroxyethyl)-3-methylphenyl]-N,N-dimethylpyridine-2-carboxamide収率 565.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  1. customThe reaction was partitioned between water and EtOAc
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-4882e27bcdcc4bd29f58af4dbe3ee4bd
出典データセット
uspto-grants-2015_12
特許番号
US09199982B2

反応ノート

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