1-Pyrrolidineethanamine → 5-Bromo-N-[2-(pyrrolidin-1-yl)ethyl]pyridin-2-amine

HRID 1916589노트

반응식

HRID 1916589 반응식
C([O-])([O-])=O.[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:54]1[CH:59]=[CH:58][C:57]([Br:60])=[CH:56][N:55]=1.[NH2:61][CH2:62][CH2:63][N:64]1[CH2:68][CH2:67][CH2:66][CH2:65]1>C1(C)C=CC=CC=1.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:60][C:57]1[CH:58]=[CH:59][C:54]([NH:61][CH2:62][CH2:63][N:64]2[CH2:68][CH2:67][CH2:66][CH2:65]2)=[N:55][CH:56]=1

참가 물질

9

반응물 4

HCID 13441-PyrrolidineethanamineHCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 634876Binap, (A+-)-

생성물 1

HCID 626427485-Bromo-N-[2-(pyrrolidin-1-yl)ethyl]pyridin-2-amine

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

13.8 g (100.0 mmol) K2CO3, 79 mg (0.12 mmol) 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and 28 mg (0.12 mmol) Pd(OAc)2 are added successively to a solution of 1.5 g (6.33 mmol) 2,5-dibromopyridine and 0.98 mL (7.60 mmol) 1-(2-aminoethyl)-pyrrolidine in 60 mL toluene. The reaction is refluxed for 40 h. The solvent is eliminated i.vac. and the residue is taken up in 150 mL EtOAc and 100 mL water. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Purification is carried out by column chromatography on silica gel (gradient: EtOAc/MeOH/NH3 19:1:0.1 to EtOAc/MeOH/NH3 9:1:0.1).

후처리

  1. temperatureThe reaction is refluxed for 40 h
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customPurification

출처 및 근거

ORD 기록
ord-7129f45d21e24b6fb1a6b29c9ffb5bd5
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

반응 노트

불러오는 중…