Iodoethane → HCID 117992935, 화합물

HRID 922580노트

반응식

HRID 922580 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([F:11])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](I)[CH3:19]>CS(C)=O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:18][CH3:19])=[C:4]([F:11])[CH:3]=1.[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([CH2:18][CH3:19])[CH:6]=2

참가 물질

6

반응물 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 247287446-Bromo-4-fluoro-1H-indazole

생성물 2

HCID 117992935HCID 117992935, 화합물수율 52%HCID 117992991HCID 117992991, 화합물수율 17%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 6-bromo-4-fluoro-1H-indazole (1000 g, 4.65 mol) in DMSO (5.0 L), was added K2CO3 (900 g, 6.51 mol), followed by addition of ethyl iodide (900 g, 5.77 mol). The reaction mixture was stirred at r.t. for 16 h. The reaction mixture was poured into ice water and extracted with EtOAc. The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography (0-10% EtOAc in hexanes) to give 6-bromo-1-ethyl-4-fluoro-1H-indazole (595 g, 2.45 mol, 52%) as a yellow oil and 6-bromo-2-ethyl-4-fluoro-2H-indazole (278 g, 1.14 mol, yield 17%) as an orange solid. 1H NMR (600 MHz, CDCl3) δ 1.52 (t, 3H), 4.39 (q, 2H), 6.95 (dd, 1H), 7.40 (s, 1H), 8.02 (s, 1H). MS (ES+)(M+H) 243.

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (0-10% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-076eb262a5ab47c4996e9acdc0648546
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278953B2

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