Bromine → HCID 59277594, compound

HRID 2097213Notes

Reaction equation

HRID 2097213 reaction equation
[Br:1]Br.[CH3:3][C@@H:4]1[NH:10][C:9]2[N:11]=[CH:12][CH:13]=[CH:14][C:8]=2[CH2:7][NH:6][C:5]1=[O:15]>C(O)(=O)C>[Br:1][C:13]1[CH:12]=[N:11][C:9]2[NH:10][C@@H:4]([CH3:3])[C:5](=[O:15])[NH:6][CH2:7][C:8]=2[CH:14]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 59277595HCID 59277595, compound

Product 1

HCID 59277594HCID 59277594, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (43 ul, 0.84 mmol) was added drop wise to a solution of (S)-2-methyl-1,2,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-3-one (136 mg, 0.77 mmol) in acetic acid (10 mL). The reaction was stirred at room temperature for 3 h. The reaction was quenched with sat. NaHCO3 (10 mL) and extracted with ethyl acetate (3×15 mL), dried over sodium sulfate and concentrated to give the title compound (140 mg, 71%): 1H NMR (400 MHz, CDCl3) δ 7.93 (s, 1H), 7.31 (s, 1H), 7.20 (b, 1H), 5.95 (bs, 1H), 4.97-4.91 (m, 1H), 4.72-4.70 (m, 1H), 3.85-3.79 (m, 1H), 1.47 (d, J=6.4 Hz, 3H).

Workup

  1. customThe reaction was quenched with sat. NaHCO3 (10 mL)
  2. extractionextracted with ethyl acetate (3×15 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-75581c2442354f2681b865712650e9b8
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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