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Sodium Carbonate → 5-Iodo-2-[4-(morpholine-4-sulfonyl)-phenyl]-imidazo[2,1-b][1,3,4]thiadiazole

HRID 2409585
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HRID 2409585 반응식
Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([I:10])[N:4]2[N:3]=1.[N:11]1([S:17]([C:20]2[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[I:10][C:9]1[N:4]2[C:5]([S:6][C:2]([C:23]3[CH:24]=[CH:25][C:20]([S:17]([N:11]4[CH2:12][CH2:13][O:14][CH2:15][CH2:16]4)(=[O:18])=[O:19])=[CH:21][CH:22]=3)=[N:3]2)=[N:7][CH:8]=1
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6

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HCID 10340Sodium CarbonateHCID 441195464-(Morpholin-4-ylsulphonyl)benzeneboronic acidHCID 662215402-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole

생성물 1

HCID 667171205-Iodo-2-[4-(morpholine-4-sulfonyl)-phenyl]-imidazo[2,1-b][1,3,4]thiadiazole수율 42.5%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물
촉매
HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (200 mg, 0.44 mmol), 4-(4-morpholinylsulfonyl)phenylboronic acid (144 mg, 0.52 mmol), PdCl2(PPh3)2 (60 mg, 0.088 mmol) and 2M aq Na2CO3 (1.2 mL) in dioxane (8 mL) was heated at 90° C. for 18 h. The solvent was removed in vacuo and the residue was triturated from EtOAc and filtered. The filtrate was evaporated and the residue was recrystallyzed from MeOH to give the desired product (89 mg, 31%) as a brown solid.

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated from EtOAc
  3. filtrationfiltered
  4. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-7540ac21b2904eb4ba1f199a14999810
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08815918B2

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