Cesium carbonate → HCID 178429941, 화합물

HRID 390713

반응식

HRID 390713 반응식
[CH3:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C:6]1[S:7][C:8]([CH3:11])=[CH:9][N:10]=1)=[O:4].ClC1C=C2C(N=CC=C2)=C2C=1C=CC=N2.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:35][C:36]1[CH:41]=[C:40](I)[CH:39]=[C:38]([Cl:43])[CH:37]=1.[OH-].[NH4+].O>CN1CCCC1=O>[Cl:35][C:36]1[CH:41]=[C:40]([N:10]2[CH:9]=[C:8]([CH3:11])[S:7]/[C:6]/2=[N:5]\[C:3](=[O:4])[C:2]([CH3:13])([CH3:12])[CH3:1])[CH:39]=[C:38]([Cl:43])[CH:37]=1

참가 물질

7

반응물 5

HCID 10796Cesium carbonateHCID 764241,3-Dichloro-5-iodobenzeneHCID 778655-Chloro-1,10-phenanthrolineHCID 171909292,2-dimethyl-N-(5-methyl-1,3-thiazol-2-yl)propanamideHCID 86589665Water ammonium hydroxide

생성물 1

HCID 178429941HCID 178429941, 화합물

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

In a 4 mL vial charged with a stir bar, 2,2-dimethyl-N-(5-methyl-1,3-thiazol-2-yl)propanamide (71 mg, 0.35 mmol) was added, followed by copper(I) trifluoromethanesulfonate benzene complex (35 mg, 0.07 mmol), 5-chloro-1,10-phenanthroline (30 mg, 0.14 mmol) and cesium carbonate (126 mg, 0.39 mmol). A loose cap with septum was placed on the vial and the vial was placed under vacuum in a vacuum oven for 30 minutes. The solid mixture was purged with nitrogen gas a couple of times. Then 1,3-dichloro-5-iodobenzene (115 mg, 0.42 mmol) dissolved in 1-methyl-2-pyrrolidinone (1.0 mL) was added to the solid mixture. The vial was capped and placed on a heater/stirrer and heated to 120° C. overnight. Then a 1 mL solution of concentrated ammonium hydroxide/water (1:2) was added. The reaction was filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (C8, gradient 10-100% acetonitrile/water/0.1% trifluoroacetic acid).

후처리

  1. additionIn a 4 mL vial charged with a stir bar
  2. customA loose cap with septum
  3. customThe solid mixture was purged with nitrogen gas a couple of times
  4. additionwas added to the solid mixture
  5. customThe vial was capped
  6. customplaced on a heater/stirrer
  7. filtrationThe reaction was filtered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by reverse phase HPLC (C8, gradient 10-100% acetonitrile/water/0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-247e4401033944dd8c4df11346919a95
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383657B2

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