N-bromobutanimide → HCID 58293758, compound

HRID 446727Notes

Reaction equation

HRID 446727 reaction equation
[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][N:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:5][C:4]=2[CH:3]=[CH:2]1.C1C(=O)N([Br:23])C(=O)C1>C(#N)C>[Br:23][C:2]1[S:1][C:10]2[CH2:9][CH2:8][CH2:7][N:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58293775HCID 58293775, compound

Product 1

HCID 58293758HCID 58293758, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Compound 1050 (1.53 g, 6.79 mmol) in acetonitrile (70 mL) at 0° C. was slowly added NBS (1.69 g, 9.48 mmol). The reaction was stirred at room temperature for 30 minutes, at which point HPLC analysis indicated disappearance of starting material. The reaction was quenched by addition of saturated sodium bicarbonate (50 mL) and stirred for one hour. The mixture was extracted with diethyl ether (3×100 mL), the volatiles removed under reduced pressure, and the residue purified by silica chromatography (0-30% ethyl acetate in hexanes) to give ethyl 2-bromo-7,8-dihydro-4H-thieno[3,2-c]azepine-5-carboxylate as a pale yellow oil (Compound 1051, 2.07 g, 86% yield); 1H NMR (300 MHz, CDCl3): δ 6.84-6.70 (m, 1H), 4.30 (d, J=15.4 Hz, 2H), 4.02 (q, J=6.7 Hz, 2H), 3.63 (s, 2H), 2.78 (dd, J=4.6, 5.7 Hz, 2H), 1.80 (s, 2H) and 1.16 (t, J=6.8 Hz, 3H).

Workup

  1. customat 0° C.
  2. customThe reaction was quenched by addition of saturated sodium bicarbonate (50 mL)
  3. stirringstirred for one hour
  4. extractionThe mixture was extracted with diethyl ether (3×100 mL)
  5. customthe volatiles removed under reduced pressure
  6. customthe residue purified by silica chromatography (0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3f22e757df4342a785f51805fb8e6d99
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

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