Hydrochloric Acid → HCID 49760969, 화합물

HRID 1619105노트

반응식

HRID 1619105 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 49760969HCID 49760969, 화합물수율 22.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-220c95d610594831a723179af6d4e3d9
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772288B2

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