Water → HCID 57500672、化合物

HRID 2174918ノート

反応式

HRID 2174918 の反応式
Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9]C)=O.Cl.N[C:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C([O-])(=O)C.[Na+].O.C[N:33](C=O)C>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]>[O:9]=[C:7]1[C:3]2[N:4]=[CH:5][S:6][C:2]=2[C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:13][C:14]=2[NH:33]1

参加物

7

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 40787018Methyl 5-bromo-1,3-thiazole-4-carboxylateHCID 67039410HCID 67039410、化合物

生成物 1

HCID 57500672HCID 57500672、化合物収率 39%

試薬・触媒・溶媒 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒

反応条件

温度
120 °C

実験手順

In a microwave vessel, methyl 5-bromothiazole-4-carboxylate (1.0 eq, 97 mg, 0.44 mmol), 2-amino-3-methoxycarbonyl phenyl boronic acid HCl (1.1 eq, 111 mg, 0.48 mmol), sodium acetate (3.0 eq, 107 mg, 1.31 mmol) and PdCl2(dppf) (0.05 eq, 11 mg, 0.022 mmol) were mixed together in anhydrous DMF (1 ml). The mixture was heated in a microwave oven at 120° C. for 10 nm. Water was added and the material extracted with CH2Cl2. The combined extracts were washed with brine, dried over Na2SO4 and the solvents removed by evaporation. The material was dissolved in a mixture of CH2Cl2 and MeOH and the solution filtered through a pad of celite. Evaporation of the volatiles afforded crude methyl 4-oxo-4,5-dihydrothiazolo[4,5-c]quinoline-7-carboxylate as a black solid (44 mg, 39% yield). A small part of the compound was subjected to preparative HPLC for analytical purpose. LCMS (ES): 95% pure, m/z 261 [M+1]+.

後処理

  1. extractionthe material extracted with CH2Cl2
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvents removed by evaporation
  5. dissolutionThe material was dissolved in a mixture of CH2Cl2 and MeOH
  6. filtrationthe solution filtered through a pad of celite
  7. customEvaporation of the volatiles

出典と根拠

ORDレコード
ord-59be9866206448baa030b1b2079777c0
出典データセット
uspto-grants-2015_06
特許番号
US09062043B2

反応ノート

読み込み中…