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

HRID 1773717ノート

反応式

HRID 1773717 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
120 °C

実験手順

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.

後処理

  1. concentrationThe reaction was concentrated under reduced pressure and purification

出典と根拠

ORDレコード
ord-f3bb7a628eb5428591b6b845e0b1bf31
出典データセット
uspto-grants-2016_02
特許番号
US09255089B2

反応ノート

読み込み中…