Toluene → HCID 57786272, 화합물

HRID 1628996노트

반응식

HRID 1628996 반응식
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[C:10]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.CC(C)([O-])C.[K+]>C(#N)C.C(OCC)(=O)C.O1CCCC1>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:19]1[C:6]2=[N:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:9]=3[N:5]2[CH2:4][CH2:3][CH:2]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 23665647Potassium tert-butoxideHCID 68775340HCID 68775340, 화합물

생성물 1

HCID 57786272HCID 57786272, 화합물수율 23%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of [1-(3-bromopropyl)-7-(diethylamino)-1H-benzimidazol-2-yl](2,4-dichlorophenyl)methanone (Reference example 211, 360 mg, 0.745 mmol) and triphenylphosphine (586 mg, 2.23 mmol) in acetonitrile (5 mL) was stirred for 60 h at 80° C. The reaction mixture was concentrated in vacuo. Toluene (5 mL), tetrahydrofuran (1 mL), and potassium tert-butoxide (85%, 83.6 mg, 0.745 mmol) was added at room temperature. After 1 h, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over sodium sulfate, filtrated, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 5-25% ethyl acetate/n-hexane gradient mixture to afford the desired product as pale yellow solid (65.5 mg, 0.170 mmol, 23%).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a 5-25% ethyl acetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-325426d0e6524bb4acd628cd514f4024
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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