Sodium Bicarbonate → 1,4-dihydro-4-(1H-indazol-5-yl)-2,6-dimethyl-3,5-pyridinedicarbonitrile

HRID 218481

反応式

HRID 218481 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[NH2:12]/[C:13](/[CH3:17])=[CH:14]\[C:15]#[N:16].C([O-])(O)=O.[Na+]>CC(O)=O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]3[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[NH:12][C:7]([CH3:6])=[C:8]3[C:9]#[N:1])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 212506441H-Indazole-5-carboxaldehyde

生成物 1

HCID 249591041,4-dihydro-4-(1H-indazol-5-yl)-2,6-dimethyl-3,5-pyridinedicarbonitrile収率 44%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 1H-indazole-5-carboxaldehyde from Synthetic Preparation 1 (447 mg, 3.1 mmol) and 3-aminocrotononitrile (526.4 mg, 6.41 mmol) in HOAc (10 mL) was kept at 110° C. for 1.5 hr, after which it was cooled to rt. The reaction was treated with NaHCO3 (sat.) to pH 10, and extracted with EtOAc. The organic phases were combined, washed with brine, and dried. Concentration followed by purification with flash chromatography afforded 1,4-dihydro-4-(1H-indazol-5-yl)-2,6-dimethyl-3,5-pyridinedicarbonitrile (370 mg, 44%) (Cpd. No. 80, Table 2). 1H-NMR (400 MHz, CDCl3): δ=8.07 (s, 1H), 7.64 (s, 1H), 7.53 (d, 1H), 7.35 (d, 1H), 4.48 (s, 1H), 2.03 (s, 6H) ppm.

後処理

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. customdried
  4. concentrationConcentration
  5. customfollowed by purification with flash chromatography

出典と根拠

ORDレコード
ord-279b7ddbe4b742d7b415f99edaec384d
出典データセット
uspto-grants-2012_06
特許番号
US08198456B2

関連ノート

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