Sodium Carbonate → N-(3-morpholin-4-yl-quinoxalin-6-yl)-2-phenyl-isobutyramide

HRID 524375ノート

反応式

HRID 524375 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:9]2)=[CH:4][CH:3]=1.[C:18]1([C:24]([CH3:44])([CH3:43])[C:25]([NH:27]C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.CCO>[N:12]1([C:8]2[CH:7]=[N:6][C:5]3[C:10]([N:9]=2)=[CH:11][C:2]([NH:27][C:25](=[O:26])[C:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH3:44])[CH3:43])=[CH:3][CH:4]=3)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 533635264-(7-Bromoquinoxalin-2-yl)morpholineHCID 586961232-phenyl-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-isobutyramide

生成物 1

HCID 67035794N-(3-morpholin-4-yl-quinoxalin-6-yl)-2-phenyl-isobutyramide収率 168.8%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 21863594Toluene ethanol溶媒

反応条件

温度
120 °C

実験手順

A mixture of 7-bromo-2-morpholin-4-yl-quinoxaline [intermediate example 2.1] (50 mg), 2-phenyl-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-isobutyramide (87 mg, 0.24 mmol) and Pd(PPh3)4 in 1:1 Toluene/EtOH (2 mL) was treated with 1M aq. sodium carbonate solution and heated at 120° C. under microwave irradiation for 15 minutes. The reaction was partitioned between EtOAc and water, the phases separated and the organic layer concentrated in vacuo. The reaction was repeated and the combined crude products were purified by trituration with DMSO to give the title compound (108 mg). UPLC-MS: RT=1.36 min; m/z (ES+) 453.27 [MH+]; required MW=452.56.

後処理

  1. customThe reaction was partitioned between EtOAc and water
  2. customthe phases separated
  3. concentrationthe organic layer concentrated in vacuo
  4. customthe combined crude products were purified by trituration with DMSO

出典と根拠

ORDレコード
ord-d0d57fc8a0b141bc9eefbe50462d506e
出典データセット
uspto-grants-2016_05
特許番号
US09340528B2

反応ノート

読み込み中…