Iodoethane → methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoate

HRID 1427226ノート

反応式

HRID 1427226 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[CH:18]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:30](I)[CH3:31].[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)([CH2:30][CH3:31])[C:19]([O:21][CH3:22])=[O:20])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 70563540methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)acetate

生成物 1

HCID 70562967methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoate収率 57%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The compound from step C (1 g, 2.4 mml) and EtI (42 mg, 2.6 mmol) were dissolved in anhydrous DMF (10 mL) Then NaH (144 mg, 3.6 mmol, 60%) was added to the mixture slowly at 0° C. After 30 minutes, the reaction mixture was quenched by saturate NH4Cl (10 mL), extracted with EA, dried over anhydrous Na2SO4, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column (PE:EA=20:1 to 5:1 to give the title compound (0.608 g, 57%). LC/MS m/z=444.1[M+H]+. The two enantiomers were separated by SFC chiral separation.

後処理

  1. customthe reaction mixture was quenched
  2. concentrationby saturate NH4Cl (10 mL)
  3. extractionextracted with EA
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column (PE

出典と根拠

ORDレコード
ord-3fb1a3d1838646e79456ea59f3785a97
出典データセット
uspto-grants-2015_01
特許番号
US08933113B2

反応ノート

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