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

HRID 391578

반응식

HRID 391578 반응식
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[N:16]([CH3:17])[N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[CH:2].Br[C:20]1[CH:21]=[N:22][CH:23]=[C:24]([CH:28]=1)[C:25]([OH:27])=[O:26].CCN(CC)CC>CN(C=O)C.CCOC(C)=O.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>[CH3:17][N:16]1[C:12]([C:10]([NH:9][C:5]2[CH:4]=[C:3]([C:1]#[C:2][C:20]3[CH:21]=[N:22][CH:23]=[C:24]([CH:28]=3)[C:25]([OH:27])=[O:26])[CH:8]=[CH:7][CH:6]=2)=[O:11])=[CH:13][C:14]([CH3:18])=[N:15]1

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 887075-Bromonicotinic acidHCID 57657904N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

생성물 1

HCID 576579595-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)-ethynyl]nicotinic acid수율 12%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

In a 50 mL round bottom flask, N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (0.888 g, 3.71 mmol) and 5-bromo nicotinic acid (0.50 g, 2.47 mmol) were dissolved in DMF (15 mL) The mixture was then degassed by bubbling N2(g) through it for ˜20 min. The mixture was then treated sequentially with NEt3 (1.37 mL, 9.90 mmol), Pd(PPh3)2Cl2 (0.173 g, 0.247 mmol) and CuI (0.094 g, 4.95 mmol). The reaction mixture was allowed to stir at 50° C. for 4 h. The reaction mixture was diluted with EtOAc (25 mL) causing a pale yellow precipitate to form. The white precipitate was filtered off giving the title compound (0.105 g, 12%).

후처리

  1. customwas then degassed
  2. customby bubbling N2(g) through it for ˜20 min
  3. customto form
  4. filtrationThe white precipitate was filtered off

출처 및 근거

ORD 기록
ord-5388f87ef62540f18dbad60e1ebbed8b
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383825B2

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