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

HRID 218481

반응식

HRID 218481 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-279b7ddbe4b742d7b415f99edaec384d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198456B2

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