Dichloromethane → 6-(3,5-dimethylisoxazol-4-yl)-4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1773717노트

반응식

HRID 1773717 반응식
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9](B3OC(C)(C)C(C)(C)O3)[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:26])[O:4][N:3]=1.Br[C:28]1[N:32]([CH2:33][CH3:34])[N:31]=[CH:30][C:29]=1[CH3:35].C(Cl)Cl.C1CCN2C(=NCCC2)CC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CS(C)=O.O>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:28]3[N:32]([CH2:33][CH3:34])[N:31]=[CH:30][C:29]=3[CH3:35])[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:26])[O:4][N:3]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1176019395-bromo-1-ethyl-4-methyl-1H-pyrazoleHCID 1232967096-(3,5-Dimethylisoxazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one

생성물 1

HCID 1176017146-(3,5-dimethylisoxazol-4-yl)-4-(1-ethyl-4-methyl-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-2(3H)-one

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 23503278(Methanesulfinyl)methane--water (1/1)용매

반응 조건

온도
120 °C

실험 절차

To a microwave vial containing 6-(3,5-dimethylisoxazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (40 mg, 0.11 mmol, 1 equiv.) were added 5-bromo-1-ethyl-4-methyl-1H-pyrazole 11 (64 mg, 0.34 mmol, 3 equiv.), Pd(dppf)Cl2. CH2Cl2 (9 mg, 0.011 mmol, 0.1 equiv.), DBU (101 μL, 6 equiv.) and DMSO-H2O (4 mL, 0.2 M, 2/1, v/v). The mixture was heated to 120° C. for 30 min in microwave. The reaction was concentrated under reduced pressure and purification was carried out by reverse phase HPLC.

후처리

  1. concentrationThe reaction was concentrated under reduced pressure and purification

출처 및 근거

ORD 기록
ord-f3bb7a628eb5428591b6b845e0b1bf31
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255089B2

반응 노트

불러오는 중…