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

HRID 1916589ノート

反応式

HRID 1916589 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7129f45d21e24b6fb1a6b29c9ffb5bd5
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

反応ノート

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