1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Bromoisoquinoline-1-carbonitrile

HRID 966914Notes

Reaction equation

HRID 966914 reaction equation
[N:1]12CCCN=C1CCCC[CH2:2]2.[Br:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[N+:15]([O-])[CH:14]=1.C([Si](C)(C)C)#N>C1COCC1>[Br:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([C:2]#[N:1])=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82115Trimethylsilyl cyanideHCID 8173234-Bromoisoquinoline N-oxide

Product 1

HCID 218749014-Bromoisoquinoline-1-carbonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (1.67 mL, 11.2 mmol) was added to a mixture of compound 470A (1.12 g, 5.00 mmol) and cyanotrimethylsilane (0.75 mL, 5.5 mmol) in 35 mL of THF. The resulting homogeneous mixture was refluxed for 20 min. After concentrating in vacuo, the residue was purified by flash chromatography on a 5×15 cm silica get column, eluting with 3:1 hexane:ethyl acetate to give 0.95 g (82%) of compound 470B as a white powder. 1H NMR (400 MHz, CDCl3): δ 8.85 (s, 1H), 8.36 (d, 1H, J=8.5 Hz), 8.28 (d, 1H, J=8.5 Hz), 7.96 (t, 1H, J=8.5 Hz), 7.89 (t, 1H, J=8.5 Hz).

Workup

  1. temperatureThe resulting homogeneous mixture was refluxed for 20 min
  2. concentrationAfter concentrating in vacuo
  3. customthe residue was purified by flash chromatography on a 5×15 cm silica
  4. customget column
  5. washeluting with 3:1 hexane

Sources & evidence

ORD record
ord-be595e9a57834d4fa45bbb8f4d6575d2
Source dataset
uspto-grants-2005_10
Patent number
US06953679B2

Reaction notes

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