Cyanogen Bromide → 1391934-97-6

HRID 1183242Notes

Reaction equation

HRID 1183242 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:3]=1/[CH:4]=[CH:5]/[C:6]1[CH:14]=[CH:13][C:9]([N:10](C)[CH3:11])=[CH:8][CH:7]=1.N#CBr>CC(C)=O>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:3]=1/[CH:4]=[CH:5]/[C:6]1[CH:14]=[CH:13][C:9]([NH:10][CH3:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 51039205FIDAS-3

Product 1

HCID 681543931391934-97-6

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1 g (3.86 mmol) of 4r and 820 mg (7.72 mmol, 2 equiv) of cyanogen bromide in 15 mL of acetone was refluxed for 16 h. The mixture was cooled and concentrated under a stream of argon. The residue was triturated with ether, and the combined ethereal extracts were combined and concentrated. The product was refluxed with 25 mL of concentrated HCl for 3 h. The mixture was neutralized with 2M NaOH solution, extracted with ether, dried over anhydrous MgSO4, and concentrated. The product was purified by chromatography using 1:5 EtOAc-hexane to afford 320 mg (34%) of 4 cc as a yellow solid: mp 51-52° C. 1H NMR (DMSO-d6): δ 7.32 (d, 2H, J=8.8 Hz), 7.29-7.21 (m, 2H), 7.14-7.06 (m, 2H), 6.79 (d, 1H, J=16.4 Hz), 6.55 (d, 2H, J=8.8 Hz), 6.02 (q, 1H, J=5.2 Hz), 2.70 (d, 3H, J=5.2 Hz). 13C NMR (DMSO-d6): δ 160.36 (dd, J1=246.8 Hz, J2=8.0 Hz, two C), 150.88, 136.35 (t, J=7.5 Hz), 128.42 (two C), 127.96 (d, J=10.7 Hz), 124.53, 115.32 (t, J=15.5 Hz), 112.33 (dd, J1=19.1 Hz, J2=6.8 Hz, two C), 112.09 (two C), 108.86, 29.93. MS: m/z (%) 246 (30), 245 (100), 244 (15). Anal. Calcd for C15H13F2N: C, 73.45; H, 5.34. Found: C, 73.31; H, 5.26.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under a stream of argon
  3. customThe residue was triturated with ether
  4. concentrationconcentrated
  5. temperatureThe product was refluxed with 25 mL of concentrated HCl for 3 h
  6. extractionextracted with ether
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customThe product was purified by chromatography
  10. customto afford 320 mg (34%) of 4 cc as a yellow solid

Sources & evidence

ORD record
ord-125331abc1694bfb8b4c0e000d145459
Source dataset
uspto-grants-2014_03
Patent number
US08664276B2

Reaction notes

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