Dichloromethane → 5-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)-1-methyl 1H-pyrazole-4-carboxamide

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]([CH3:33])[N:31]=[CH:30][C:29]=1[C:34]#[N:35].C(Cl)Cl.C1CCN2C(=NCCC2)CC1.CS(C)=[O:52].O>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]>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:28]3[N:32]([CH3:33])[N:31]=[CH:30][C:29]=3[C:34]([NH2:35])=[O:52])[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

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 (100 mg, 0.28 mmol, 1 equiv.) was added 5-bromo-1-methyl-1H-pyrazole-4-carbonitrile (130 mg, 0.30 mmol, 2.5 equiv.), Pd(dppf)Cl2.CH2Cl2 (23 mg, 0.03 mmol, 0.1 equiv.) and DBU (253 μL, 1.69 mmol, 6 equiv.) and dissolved in 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 in vacuo and purification was then carried out by reverse phase HPLC.

後処理

concentrationThe reaction was concentrated in vacuo and purification

出典と根拠

ORDレコード: ord-3060c97c352f4e109e4f5dfcb7340b10
出典データセット: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09255089B2

反応ノート

読み込み中…

反応式

参加物

反応物 5

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

反応ノート