N-bromobutanimide → HCID 22051019, compound

HRID 1867126Notes

Reaction equation

HRID 1867126 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[F:23])[C:8](=[O:24])[CH:7]=1.[Br:30]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>>[Br:30][C:7]1[C:8](=[O:24])[N:9]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[F:23])[C:10]([CH3:12])=[CH:11][C:6]=1[O:5][CH2:4][C:3]1[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 22049960HCID 22049960, compound

Product 1

HCID 22051019HCID 22051019, compoundYield 59%

Procedure

A 100 mL round bottomed flask equipped with stirbar and nitrogen inlet was charged with the product of Step 4 (2.15 g, 5.3 mmol) and N-methyl-2-pyrrolidine (15 mL). After cooling to 0 C, a solution of N-bromo succinimide (1.03 g, 5.8 mmol) in 10 mL of N-methyl-2-pyrrolidine was added over 15 minutes. After 15 additional minutes, the reaction mixture was warmed to room temperature and was stirred for 1 hour. The mixture was then poured into saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer was washed with brine and concentrated in vacuo. The residue was triturated with acetonitrile and filtered to give the title compound as a white powder (1.5 g, 59%). 1H NMR (400 MHz, CD3OD) δ 8.00 (dd, J=2.0 and 8.4 Hz, 1H), 7.95 (dd, J=1.7 and 10 Hz, 1H), 7.64 (q, J=8.8 and 14.4 Hz, 1H), 7.51 (t, J=7.6 Hz, 1H), 7.04 (t, J=8.4 Hz, 2H), 6.66 (s, 1H), 5.36 (s, 2H), 3.95 (s, 3H), 2.01 (s, 3H) ppm. 19F NMR (400 MHz, CD3OD) δ −111.50 (1F), −115.97 (1F), −123.01 (1F) ppm. ES-HRMS m/z 484.0169 (M+H calcd for C21H16BrF3NO4 requires 484.0192).

Workup

  1. customA 100 mL round bottomed flask equipped with stirbar and nitrogen inlet
  2. temperatureAfter cooling to 0 C
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with acetonitrile
  7. filtrationfiltered

Sources & evidence

ORD record
ord-fe13b307294b4bc39b448dadd3d61f29
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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