Water → 5-Iodo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazole

HRID 422070

反応式

HRID 422070 の反応式
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.[I:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][N:15]=[CH:14]2.C([O-])([O-])=O.[Cs+].[Cs+].O>CS(C)=O>[I:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)[N:15]=[CH:14]2

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 218947395-Iodo-1H-indazole

生成物 1

HCID 580155445-Iodo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazole収率 52.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
25 °C

実験手順

1-(2-Chloroethyl)pyrrolidine hydrochloride (9.88 g, 58.1 mmol) was added to a suspension of 5-iodo-1H-indazole (8.86 g, 36.3 mmol) and Cs2CO3 (50.8 g, 456 mmol) in anhydrous DMSO (100 mL) and the resulting suspension was stirred at 25° C. for 14 h. H2O (100 mL) was added and the aqueous solution was extracted with EtOAc (3×200 mL). The combined organic extracts were washed with brine (2×200 mL), dried over MgSO4 and concentrated under reduced pressure. Flash chromatography on silica gel (9:1 Et2O/Et3N) afforded 6.473 g (52%) of the title compound as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.08 (br d, J=13 Hz, 1H), 7.91 (d, J=0.9 Hz, 1H), 7.60 (dd, J=87, 1.3 Hz, 1H), 7.25 (d, J=8.7 Hz, 1H), 4.50 (t, J=7.4 Hz, 2H), 2.98 (t, J=7.4 Hz, 2H), 2.59-2.50 (m, 4H), 1.82-1.70 (m, 4H).

後処理

  1. extractionthe aqueous solution was extracted with EtOAc (3×200 mL)
  2. washThe combined organic extracts were washed with brine (2×200 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a9ea4691af474979b04bf4a15292f509
出典データセット
uspto-grants-2012_01
特許番号
US08101632B2

関連ノート

読み込み中…