Hydrochloric Acid → HCID 49760969、化合物

HRID 1619105ノート

反応式

HRID 1619105 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:11][C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][C:17](=[O:21])[NH:18]2)=[CH:14][CH:13]=1.Cl[CH2:23][CH2:24][N:25]([CH2:33][CH2:34]Cl)[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].Cl>O1CCCC1>[Br:11][C:12]1[CH:20]=[C:19]2[NH:18][C:17](=[O:21])[C:16]3([CH2:34][CH2:33][N:25]([C:26]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:32])[CH2:24][CH2:23]3)[C:15]2=[CH:14][CH:13]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 27732896-bromo-2,3-dihydro-1H-indol-2-oneHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

生成物 1

HCID 49760969HCID 49760969、化合物収率 22.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Lithium bis(trimethylsilyl)amide (1.0M in tetrahydrofuran, 2.80 mL, 2.80 mmol) was added dropwise to a stirred suspension of 6-bromoindolin-2-one (preparation 1, 0.20 g, 0.94 mmol) in tetrahydrofuran (1.5 mL) at 0° C. The mixture was stirred for 15 minutes, then tert-butyl bis(2-chloroethyl)carbamate (0.25 g, 1.04 mmol) in THF (1 mL) was added dropwise and the mixture was warmed to room temperature. After stirring overnight, 2M aqueous hydrochloric acid was added to the reaction and the mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (5:1 hexanes/ethyl acetate) gave the title compound (0.08 g, 22%) as a yellow solid.

後処理

  1. stirringAfter stirring overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customPurification of the residue by flash chromatography (5:1 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-220c95d610594831a723179af6d4e3d9
出典データセット
uspto-grants-2014_07
特許番号
US08772288B2

反応ノート

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