Iodoethane → HCID 117992935、化合物

HRID 922580ノート

反応式

HRID 922580 の反応式
[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

参加物

6

反応物 3

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

生成物 2

HCID 117992935HCID 117992935、化合物収率 52%HCID 117992991HCID 117992991、化合物収率 17%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-076eb262a5ab47c4996e9acdc0648546
出典データセット
uspto-grants-2016_03
特許番号
US09278953B2

反応ノート

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