Triethylamine → HCID 59635506, 화합물

HRID 383700노트

반응식

HRID 383700 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([CH:11]=[O:12])=[C:4]2[N:3]=1.[C:13]([C:16]1[S:20][C:19](B(O)O)=[CH:18][CH:17]=1)([OH:15])=[O:14].C(N(CC)CC)C>CN(C=O)C>[CH:11]([C:10]1[CH:9]=[N:8][N:5]2[CH:6]=[CH:7][C:2]([C:19]3[S:20][C:16]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=3)=[N:3][C:4]=12)=[O:12]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27798075-Boronothiophene-2-carboxylic acidHCID 581964015-Chloropyrazolo(1,5-a)pyrimidine-3-carbaldehyde

생성물 1

HCID 59635506HCID 59635506, 화합물수율 22%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To 5-chloropyrazolo[1,5-a]pyrimidine-3-carbaldehyde (590 mg, 3.25 mmol) in DMF was added 5-Carboxythiophene-2-boronic acid (670 mg, 3.9 mmol), triethylamine (1.13 mL, 8.11 mmol) and dichloro-((bis-diphenylphosphino)ferrocenyl)palladium(II) dichloromethane adduct (120 mg, 0.16 mmol). The reaction mixture was degassed with nitrogen then heated at 100° C. for 2 hours. The mixture was cooled to room temperature, diluted with 1N HCl, and filtered. The collected solid was washed with 1N HCl and dried under vacuum. The desired product, 5-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid, was recovered in 22% yield and used for the next step without further purification. LCMS (M+1=274)

후처리

  1. customThe reaction mixture was degassed with nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. additiondiluted with 1N HCl
  4. filtrationfiltered
  5. washThe collected solid was washed with 1N HCl
  6. customdried under vacuum
  7. customThe desired product, 5-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)thiophene-2-carboxylic acid, was recovered in 22% yield
  8. customused for the next step without further purification

출처 및 근거

ORD 기록
ord-c458f6ad621e4135b78eb5bc1a785b9a
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367681B2

반응 노트

불러오는 중…