Potassium Carbonate → 3-Cyclopropyl-3-(4-(7-(6-methylpyridin-3-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1853003노트

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HRID 1853003 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([CH:13]([CH:17]3[CH2:19][CH2:18]3)[CH2:14][C:15]#[N:16])[CH:12]=2)[N:5]2[CH:20]=[CH:21][N:22]=[C:4]2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:29][C:30]1[N:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+]>O1CCOCC1.C(O[Pd]OC(=O)C)(=O)C>[CH:17]1([CH:13]([N:11]2[CH:12]=[C:8]([C:6]3[N:5]4[CH:20]=[CH:21][N:22]=[C:4]4[CH:3]=[C:2]([C:33]4[CH:34]=[N:35][C:30]([CH3:29])=[CH:31][CH:32]=4)[N:7]=3)[CH:9]=[N:10]2)[CH2:14][C:15]#[N:16])[CH2:19][CH2:18]1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 27630812-Methylpyridine-5-boronic acidHCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonateHCID 866853033-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-cyclopropylpropanenitrile

생성물 1

HCID 866853133-Cyclopropyl-3-(4-(7-(6-methylpyridin-3-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile수율 34%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To 3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-cyclopropyl-propanenitrile (Preparation M; 50 mg, 0.16 mmol) in dioxane (5 mL) was added K2CO3 (66 mg, 0.48 mmol), diacetoxypalladium (1.8 mg, 0.0080 mmol), 6-methylpyridin-3-ylboronic acid (44 mg, 0.32 mmol) and sodium 2′-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate (8.2 mg, 0.016 mmol). The reaction mixture was degassed with argon, sealed and heated to 80° C. for 5 hours. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH 10:1) to give the final product (20 mg, 34% yield). MS (apci) m/z=370.2 (M+H).

후처리

  1. customThe reaction mixture was degassed with argon
  2. customsealed
  3. temperatureThe reaction was cooled to ambient temperature
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (DCM/MeOH 10:1)

출처 및 근거

ORD 기록
ord-9eee707b98484269b64b37677170f1cc
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962596B2

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