Cesium carbonate → HCID 66832355, 화합물

HRID 1914527

반응식

HRID 1914527 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:9]=1)[C:5]#[N:6].[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.O1CCOCC1>[N:10]1([C:8]2[CH:7]=[C:4]([CH:3]=[C:2]([C:20]3[CH:21]=[CH:22][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=3)[N:9]=2)[C:5]#[N:6])[CH2:14][CH2:13][CH2:12][CH2:11]1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 830745802-Chloro-6-(pyrrolidin-1-yl)pyridine-4-carbonitrile

생성물 1

HCID 66832355HCID 66832355, 화합물수율 92%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

2-Chloro-6-pyrrolidin-1-yl-isonicotinonitrile (0.18 g, 0.87 mmol), 4-trifluoromethylphenylboronic acid (0.18 g, 0.95 mmol), palladium acetate (3.9 mg, 0.02 mmol), cesium carbonate (0.56 g, 1.73 mmol), and XPhos (17 mg, 0.04 mmol) were combined, placed under a nitrogen atmosphere and dioxane (1.0 mL) was added. The reaction vessel was sealed and heated to 100° C. for 2 hours. The reaction mixture was cooled to rt, filtered through celite, concentrated under reduced pressure and purified by flash column chromatography (0%-80% EtOAc in hexane) to provide the desired product (253 mg, 92%). 1H NMR (400 MHz, CDCl3) δ 8.11 (d, J=8.1 Hz, 2H), 7.70 (d, J=8.2 Hz, 2H), 7.15 (d, J=0.8 Hz, 1H), 6.54 (d, J=0.9 Hz, 1H), 3.55 (bs, 4H), 2.13-1.99 (m, 4H).

후처리

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationfiltered through celite
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash column chromatography (0%-80% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-6a7a22c1c5774919996decbdd2dafcfb
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614201B2

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