Hydrochloric Acid → HCID 49760969, compound

HRID 1619105Notes

Reaction equation

HRID 1619105 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 49760969HCID 49760969, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-220c95d610594831a723179af6d4e3d9
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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