Potassium Carbonate → 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-[4-(4-methyl-2-oxo-1-piperazinyl)phenyl]-1H-indole-7-carboxamide

HRID 1806486ノート

反応式

HRID 1806486 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH2:16][CH2:15]1.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][C:35](B3OC(C)(C)C(C)(C)O3)=[CH:34][CH:33]=2)[C:28](=[O:47])[CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)[C-]1C=CC=C1CN(C)C.[CH-]1C=CC=C1.[Fe+2]>[CH2:23]([S:20]([N:17]1[CH2:18][CH2:19][CH:14]([C:5]2[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=[C:2]([C:35]4[CH:34]=[CH:33][C:32]([N:29]5[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][C:28]5=[O:47])=[CH:37][CH:36]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:15][CH2:16]1)(=[O:22])=[O:21])[CH3:24]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 113844275-bromo-3-[1-(ethanesulfonyl)-4-piperidinyl]-1H-indole-7-carboxamideHCID 667228024-Methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-2-one

生成物 1

HCID 577326733-[1-(ethylsulfonyl)-4-piperidinyl]-5-[4-(4-methyl-2-oxo-1-piperazinyl)phenyl]-1H-indole-7-carboxamide収率 8%

試薬・触媒・溶媒 3

HCID 178483166HCID 178483166、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
160 °C

実験手順

To 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (20 mg, 0.048 mmol) was added 4-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-piperazinone (31 mg, 0.097 mmol) in dioxane (3.0 mL) and H2O (1.0 mL), potassium carbonate (13 mg, 0.097 mmol) and chloro(di-2-norbornylphosphino)(2-dimethylaminomethylferrocen-1-yl)palladium (II) (10 mg, 0.016 mmol). The reaction mixture was reacted in a microwave at 160° C. for 10 min. The reaction mixture was heated in a microwave at 160° C. for 10 min. The reaction mixture was concentrated under Nitrogen and purified by Gilson Preparatory HPLC. The desired fraction in CH3CN and H2O was treated with saturated potassium carbonate to neutralize salts and then concentrated to give 1.9 mg the title compound (8%).

後処理

  1. customThe reaction mixture was reacted in a microwave at 160° C. for 10 min
  2. concentrationThe reaction mixture was concentrated under Nitrogen
  3. custompurified by Gilson Preparatory HPLC
  4. additionThe desired fraction in CH3CN and H2O was treated with saturated potassium carbonate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-cf0862f716ab42c78b8843b20c89540e
出典データセット
uspto-grants-2013_01
特許番号
US08354406B2

反応ノート

読み込み中…