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Triethylamine → methyl 6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinate

HRID 607484
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HRID 607484 반응식
[NH2:1][C:2]1[C:11](I)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[C:13]([C:15]1[CH:16]=[C:17]([NH:21][C:22]([C:24]2[N:28]([CH3:29])[N:27]=[C:26]([CH3:30])[CH:25]=2)=[O:23])[CH:18]=[CH:19][CH:20]=1)#[CH:14].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[C:11]([C:14]#[C:13][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([C:24]3[N:28]([CH3:29])[N:27]=[C:26]([CH3:30])[CH:25]=3)=[O:23])[CH:16]=2)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1
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참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 15350913Methyl 6-amino-5-iodopyridine-3-carboxylateHCID 57657904N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

생성물 1

HCID 57657963methyl 6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinate수율 78.3%

시약·촉매·용매 4

HCID 11776Triphenylphosphine
촉매
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 6228Dimethylformamide용매

실험 절차

A mixture of methyl 6-amino-5-iodonicotinate (111 mg, 0.40 mmol), N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (144 mg, 0.60 mmol), triethylamine (0.167 ml, 1.2 mmol), dichlorobis(triphenylphosphine)palladium(II) (23 mg, 0.032 mmol) and triphenylphosphine (5.2 mg, 0.020 mmol) in 3.2 ml DMF at room temperature was degassed using vacuum and a balloon of H2, then copper(I) iodide (3.8 mg, 0.020 mmol) added. The reaction was heated at 60□ C. for 1 hour 40 minutes, then partitioned between EtOAc and dilute brine. The EtOAc layer was dried with anhydrous Na2SO4 and rotary evaporated. The solid was recrystallized from EtOAc/hexane to give the title compound as a yellow-tan solid (122 mg, 78%).

후처리

  1. customwas degassed
  2. temperatureThe reaction was heated at 60□ C
  3. custompartitioned between EtOAc and dilute brine
  4. dry with materialThe EtOAc layer was dried with anhydrous Na2SO4 and rotary evaporated
  5. customThe solid was recrystallized from EtOAc/hexane

출처 및 근거

ORD 기록
ord-57f06e5c8123482a9b5a7d21bc0b8c39
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07915443B2

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