1-Bromo-3,5-bis(trifluoromethyl)benzene → 4-(3,5-Bis(trifluoromethyl)phenyl)-6-propylpyrimidine-2-carbonitrile

HRID 733169노트

반응식

HRID 733169 반응식
[CH2:1]([C:4]1[CH:9]=[C:8]([Sn](C)(C)C)[N:7]=[C:6]([C:14]#[N:15])[N:5]=1)[CH2:2][CH3:3].[F:16][C:17]([F:30])([F:29])[C:18]1[CH:19]=[C:20](Br)[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1>CN(C)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>[F:16][C:17]([F:30])([F:29])[C:18]1[CH:19]=[C:20]([C:8]2[CH:9]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]=[C:6]([C:14]#[N:15])[N:7]=2)[CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1

참가 물질

5

반응물 2

HCID 676021-Bromo-3,5-bis(trifluoromethyl)benzeneHCID 690493004-Propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile

생성물 1

HCID 498624214-(3,5-Bis(trifluoromethyl)phenyl)-6-propylpyrimidine-2-carbonitrile수율 35.1%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

Bis(triphenylphosphine)palladium dichloride (34 mg, 0.05 mmol) was added under a nitrogen atmosphere to a mixture of 4-propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile (155 mg, 0.50 mmol) and 3,5-bis-trifluoromethyl-bromobenzene (0.10 mL, 0.58 mmol) in dimethylformamide (3 mL). The mixture was refluxed for 4 hours then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent: DCM) to afford a solid which was triturated in pentane. After filtration, 4-(3,5-bis-trifluoromethyl-phenyl)-6-propyl-pyrimidine-2-carbonitrile (63 mg, 35%) was obtained as an off white solid (mp=112° C.).

후처리

  1. temperatureThe mixture was refluxed for 4 hours
  2. concentrationthen concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. concentrationThe combined organic layers were concentrated under reduced pressure
  6. customThe residue was chromatographed over silica gel (eluent: DCM)
  7. customto afford a solid which
  8. customwas triturated in pentane
  9. filtrationAfter filtration

출처 및 근거

ORD 기록
ord-325d58f3933544e78d8062c1a27aa91d
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589095B2

반응 노트

불러오는 중…