Acetonitrile → HCID 66892282, compound

HRID 448597Notes

Reaction equation

HRID 448597 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16](Cl)[CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[Br:21]Br.[H-].[Na+].[CH3:25][S:26]([C:29]1[CH:30]=[C:31]2[C:35](=[CH:36][CH:37]=1)[NH:34][CH2:33][CH2:32]2)(=[O:28])=[O:27].[C:38](#[N:40])[CH3:39]>CN(C=O)C>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([Br:21])=[CH:18][N:17]=[C:16]([N:34]3[C:35]4[C:31](=[CH:30][C:29]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:37][CH:36]=4)[CH2:32][CH2:33]3)[CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([O:13][C:14]2[C:19]([Br:21])=[C:18]([N:34]3[C:35]4[C:31](=[CH:30][C:29]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:37][CH:36]=4)[CH2:32][CH2:33]3)[CH:39]=[CH:38][N:40]=2)[CH2:11][CH2:12]1)=[O:6])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 6342AcetonitrileHCID 24408BromineHCID 24758Sodium hydrideHCID 27361365-(Methanesulfonyl)-2,3-dihydro-1H-indoleHCID 86626960HCID 86626960, compound

Product 2

HCID 66892282HCID 66892282, compoundHCID 66894571HCID 66894571, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10a (0.15 g, 0.5 mmol) in 2 mL of acetonitrile, was added bromine (0.1 mL, 1.95 mmol). The mixture was stirred at room temperature for 6 h then evaporated. The residue was added to a pre-stirred suspension of NaH (60% in oil, 9 mg, 0.22 mmol) and 5-methanesulfonyl-2,3-dihydro-1H-indole (43 mg, 0.22 mmol) in 1 mL of DMF. The mixture was stirred at 90° C. for 12 h, quenched with water, extracted with ethyl acetate and evaporated. The residue was purified by silica gel chromatography (eluent: 20% ethyl acetate in hexane) to afford 24a and 24b (80 mg of the less polar product and 55 mg of the more polar product).

Workup

  1. customthen evaporated
  2. stirringThe mixture was stirred at 90° C. for 12 h
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. customevaporated
  6. customThe residue was purified by silica gel chromatography (eluent: 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4101a189533d482f8621bcf5d836b0bd
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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