Sodium Carbonate → 4-Ethynyl-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

HRID 625314노트

반응식

HRID 625314 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]#[C:9][Si](C)(C)C)[CH:5]=[CH:4][N:3]=1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1)([O-:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC>[C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:22]2[CH:21]=[C:20]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[CH:19]=[CH:18][C:17]=2[N+:14]([O-:16])=[O:15])[CH:7]=1)#[CH:9]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 219853912-Chloro-4-(2-(trimethylsilyl)ethynyl)pyridineHCID 66587487HCID 66587487, 화합물

생성물 1

HCID 867059454-Ethynyl-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
75 °C

실험 절차

A degassed mixture of 2-chloro-4-((trimethylsilyl)ethynyl)pyridine 24a, boronic ester 1.1e, 4.9 mL of 2 M aqueous Na2CO3, and 12 mL of DME was treated with 45 mg of XPHOS and 11 mg of Pd(OAc)2. The mixture was stirred at 75° C. for 1.5 h. The solvent was evaporated at reduced pressure and the residue was dissolved in 100 mL of dichloromethane. The solution was washed with water and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel chromatography eluting with a 0-20% gradient of EtOAc in CH2Cl2 to give 275 mg of product. MS (ESI, m/z) 308.1 [M+H]+.

후처리

  1. customThe solvent was evaporated at reduced pressure
  2. dissolutionthe residue was dissolved in 100 mL of dichloromethane
  3. washThe solution was washed with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography
  7. washeluting with a 0-20% gradient of EtOAc in CH2Cl2

출처 및 근거

ORD 기록
ord-eadab80a4581427493ae6d34dd764d22
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09301951B2

반응 노트

불러오는 중…