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Potassium Phosphate, Tribasic → HCID 59392849、化合物

HRID 216732
ノート
印刷プレビュー

反応式

HRID 216732 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[CH:8]=[N:7]2.[CH2:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[CH:28]=[CH:27][C:26](B3OC(C)(C)C(C)(C)O3)=[CH:25][C:24]=2[CH3:38])=[O:22])[CH2:17][CH2:16]1)[CH3:14].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:26]1[CH:27]=[CH:28][C:23]([C:21]([N:18]3[CH2:19][CH2:20][N:15]([CH2:13][CH3:14])[CH2:16][CH2:17]3)=[O:22])=[C:24]([CH3:38])[CH:25]=1)[CH:8]=[N:7]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 593926708-Bromo-2-chloroquinoxalineHCID 59392740HCID 59392740、化合物

生成物 1

HCID 59392849HCID 59392849、化合物

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
105 °C

実験手順

A microwave tube is charged with 8-Bromo-2-chloro-quinoxaline (Step 1.4, 298 mg, 1.226 mmol), (4-Ethyl-piperazin-1-yl)-[2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone (439 mg, 1.226 mmol), K3PO4 (532 mg, 2.450 mmol) and Pd(PPh3)4 (43.8 mg, 0.0368 mmol). After several cycles of vacuum/purge with argon, 5 ml of dry DMA are added. The reaction mixture is then heated to 105° C. for 4 h. After cooling, the suspension is poured onto 70 ml de-ionized water and filtered. The cake is re-taken in EtOAc, washed with saturated brine and dried over Na2SO4. After filtration, the mixture is concentrated in vacuo. The residue is purified by chromatography (silicagel, CH2Cl2/CH2Cl2:EtOH:NH3 90:9:1 from 1:0=>0:1) to afford the title compound as a pale brown foam, Rt=0.833 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 439 (M+1, 79Br)+.

後処理

  1. customAfter several cycles of vacuum/purge with argon, 5 ml of dry DMA
  2. additionare added
  3. temperatureAfter cooling
  4. additionthe suspension is poured onto 70 ml de-ionized water
  5. filtrationfiltered
  6. washwashed with saturated brine
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration
  9. concentrationthe mixture is concentrated in vacuo
  10. customThe residue is purified by chromatography (silicagel, CH2Cl2/CH2Cl2:EtOH:NH3 90:9:1 from 1:0=>0:1)

出典と根拠

ORDレコード
ord-173a341e7dae4de0a74121e0b62f96e1
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08193189B2

反応ノート

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