N-bromobutanimide → 5-Bromoindoline-6-carbonitrile

HRID 1054593Notes

Reaction equation

HRID 1054593 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:19])C(=O)C1.C(=O)(O)[O-].[Na+]>CC#N>[Br:19][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][C:7]=1[C:10]#[N:11])[NH:1][CH2:2][CH2:3]2

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 162444472,3-Dihydro-1H-indole-6-carbonitrile

Product 1

HCID 866985955-Bromoindoline-6-carbonitrileYield 58.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,3-dihydro-1H-indole-6-carbonitrile (2.5 g, 17.34 mmol) in MeCN (69 mL) was cooled to 0° C. and treated with NBS (3310 mg, 17.7 mmol). The light red reaction mixture was stirred at room temperature for 20 minutes, and was then poured into saturated aqueous sodium bicarbonate (200 mL). The product was extracted with ethyl acetate (2×200 mL), and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified using flash chromatography eluting with heptanes/ethyl acetate (95:5 to 60:40) to give the title compound (2.26 g, 58%) as a white solid. MS (ES−): 219.0, 221.0 (79Br M+H, 81Br M+H).

Workup

  1. customThe light red reaction mixture
  2. extractionThe product was extracted with ethyl acetate (2×200 mL)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified
  7. washeluting with heptanes/ethyl acetate (95:5 to 60:40)

Sources & evidence

ORD record
ord-6518ad69ccb1489c92121d67399d8c6e
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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