Sodium hydride → {6-[1-(5-tert-Butyl-isoxazol-3-ylcarbamoyl)-4-fluoro-2-methyl-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl}-methyl-carbamic acid tert-butyl ester

HRID 450288ノート

反応式

HRID 450288 の反応式
[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([O:16][C:17]2[C:18]([F:27])=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21]([CH3:26])=[CH:20]3)[N:13]=[CH:12][N:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C1([O:37][C:38](=O)[NH:39][C:40]2[CH:44]=[C:43]([C:45]([CH3:48])([CH3:47])[CH3:46])[O:42][N:41]=2)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:9][C:10]1[CH:15]=[C:14]([O:16][C:17]2[C:18]([F:27])=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([C:38](=[O:37])[NH:39][C:40]2[CH:44]=[C:43]([C:45]([CH3:47])([CH3:46])[CH3:48])[O:42][N:41]=2)[C:21]([CH3:26])=[CH:20]3)[N:13]=[CH:12][N:11]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 13489605Phenyl 5-tert-butylisoxazol-3-ylcarbamateHCID 59394039[6-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-pyrimidin-4-ylmethyl]-methyl-carbamic acid tert-butyl ester

生成物 1

HCID 59394696{6-[1-(5-tert-Butyl-isoxazol-3-ylcarbamoyl)-4-fluoro-2-methyl-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl}-methyl-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of [6-(4-fluoro-2-methyl-1H-indol-5-yloxy)-pyrimidin-4-ylmethyl]-methyl-carbamic acid tert-butyl ester (275 mg, 0.712 mmol) in THF (7 mL), NaH (85 mg, 2.13 mmol) is added under nitrogen at 0° C. The resulting mixture is stirred for 2 h. Then (5-tert-butyl-isoxazol-3-yl)-carbamic acid phenyl ester (370 mg, 1.42 mmol) is added to this mixture. The resulting mixture is allowed to warm to rt and stir for 18 h. The mixture is then quenched with saturated aqueous ammonium chloride. The aqueous phase is extracted with EtOAc (2×). The combined organic layers are washed with brine, dried over anhydrous sodium sulphate, concentrated and purified by FCC (0-70% EtOAc/heptane) to provide the title compound. MS (ESI) m/z 553.1 (M+1).

後処理

  1. stirringstir for 18 h
  2. customThe mixture is then quenched with saturated aqueous ammonium chloride
  3. extractionThe aqueous phase is extracted with EtOAc (2×)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. custompurified by FCC (0-70% EtOAc/heptane)

出典と根拠

ORDレコード
ord-3596e3da823a4ea9a0fba725a39ec0da
出典データセット
uspto-grants-2013_07
特許番号
US08486954B2

反応ノート

読み込み中…