N-bromobutanimide → HCID 66823802, compound

HRID 1910097Notes

Reaction equation

HRID 1910097 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C1C(=O)N([Br:25])C(=O)C1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:25][C:10]1[C:2]([Cl:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5][CH2:4]2

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 66823630tert-Butyl 4-chloro-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 66823802HCID 66823802, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl 4-chloro-2,3-dihydro-1H-indole-1-carboxylate (6.36 g, 25.07 mmol) in Dichloromethane (DCM) (100 mL) was added a solution of NBS (4.91 g, 27.6 mmol) in Dichloromethane (DCM) (200 mL). The reaction was stirred at room temperature for 2 hours. LCMS indicated good conversion, so the reaction mixture was poured into sodium bicarbonate (sat., 300 mL), and separated. The aqueous layer was extracted with ethyl acetate (2×300 mL). The combined organics were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (0-30% EtOAc in hexanes, 200 g silica gel column) to afford 1,1-dimethylethyl 5-bromo-4-chloro-2,3-dihydro-1H-indole-1-carboxylate (5.5 g) as an off-white solid. LC-MS (ES) m/z=276, 278 [M+H-t-Bu]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (s, 9H), 3.01-3.18 (m, 2H), 3.88-4.03 (m, 2H), 7.50-7.58 (m, 2H).

Workup

  1. customseparated
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×300 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (0-30% EtOAc in hexanes, 200 g silica gel column)

Sources & evidence

ORD record
ord-432580d87220480987b1fc707eedf9ec
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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