Water → HCID 117993037, 화합물

HRID 922582노트

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HRID 922582 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([Cl:11])[CH:3]=1.O.[OH-].[Cs+].[CH3:15]I.O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:15])=[C:4]([Cl:11])[CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 23679066Caesium hydroxide--water (1/1/1)HCID 247280986-Bromo-4-chloro-1H-indazole

생성물 1

HCID 117993037HCID 117993037, 화합물수율 62%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of 6-bromo-4-chloro-1H-indazole (4.0 g, 17.4 mmol), cesium hydroxide monohydrate (23.3 g, 139 mmol), tetrabutylammonium hydrogensulfate (1.36 g, 3.99 mmol) in anhydrous THF (80 mL) was added a solution of methyl iodide (9.86 g, 69.4 mmol) in THF (10 mL) dropwise at r.t. The reaction mixture was stirred for 15 min at r.t. Water was added to the reaction mixture, and the aqueous layer was extracted with EtOAc. The organic layer was concentrated, and the crude reside was purified by silica gel column chromatography (EtOAc/Heptane 0 to 100% gradient as eluent) to afford 6-Bromo-4-chloro-1-methyl-1H-indazole (2.65 g, 62%). 1H NMR (600 MHz, methanol-d4) δ 4.05 (s, 3H), 7.32 (d, 1H), 7.79 (s, 1H), 8.03 (s, 1H).

후처리

  1. extractionthe aqueous layer was extracted with EtOAc
  2. concentrationThe organic layer was concentrated
  3. customthe crude reside was purified by silica gel column chromatography (EtOAc/Heptane 0 to 100% gradient as eluent)

출처 및 근거

ORD 기록
ord-2c9b8e943a9c40038517396a17c26fc1
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278953B2

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