Water → HCID 57500672, 화합물

HRID 1919654노트

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HRID 1919654 반응식
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

참가 물질

7

반응물 5

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

생성물 1

HCID 57500672HCID 57500672, 화합물수율 39%

시약·촉매·용매 1

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

반응 조건

온도
120 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-37f6558c650444b488cbfe6f4cc6df19
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168651B2

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