N-bromobutanimide → HCID 21081597, compound

HRID 2117151Notes

Reaction equation

HRID 2117151 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:6]=12.C1C(=O)N([Br:36])C(=O)C1>C(#N)C>[Br:36][C:13]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]2[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:2]=2[F:1])[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21081635HCID 21081635, compound

Product 1

HCID 21081597HCID 21081597, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (2.40 g, 5.96 mmol) in 20 mL of acetonitrile at 0° C. was added a solution of NBS (1.01 g, 5.69 mmol, Aldrich) in 10 mL of acetonitrile. The reaction mixture was stirred at 0° C. for 30 min, quenched by the addition of cold water (50 mL), and extracted with EtOAc (3×120 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, eluting with dichloromethane) to afford the desired product (2.70 g, 94%) as a light yellow oil. MS(ESI+) m/z 482.9 (M+H)+.

Workup

  1. customquenched by the addition of cold water (50 mL)
  2. extractionextracted with EtOAc (3×120 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (SiO2, eluting with dichloromethane)

Sources & evidence

ORD record
ord-476077cc2ff3458796bd2762ba03f378
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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