Azobisisobutyronitrile → HCID 66677503, compound

HRID 2404357Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[CH3:10])[C:5]#[N:6].CC(N=NC(C#N)(C)C)(C#N)C.BrN1C(=O)CCC1=O.Cl.[C:33]([O:37][C:38](=[O:42])[CH2:39][NH:40][CH3:41])([CH3:36])([CH3:35])[CH3:34].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:5]([C:4]1[CH:3]=[C:2]([F:1])[C:9]([CH2:10][N:40]([CH3:41])[CH2:39][C:38]([O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:42])=[C:8]([F:11])[CH:7]=1)#[N:6]

Participants

Conditions

Temperature: 90 °C

Procedure

To a degassed solution of 3,5-difluoro-4-methylbenzonitrile (1.53 g, 10 mmol) and AIBN (0.033 g; 0.20 mmol) in ACN (40 mL) was added N-bromo-succinimide (2.14 g, 12.0 mmol). The reaction mixture was heated at 90° C. for 24 hours. The solvent was evaporated in vacuo and the residue partitioned between water and DCM. The organic phase was passed through a hydrophobic frit and the solvent evaporated in vacuo. The residue was dissolved in CAN, and then sarcosine t-butyl ester hydrochloride (1.09 g, 6.0 mmol) and K2CO3 (2.07 g, 15 mmol) added. The reaction mixture was stirred at 70° C. for 18 hours. The suspension was filtered and the filtrate evaporated in vacuo. The residue was purified by flash chromatography (silica, iso-hexane/EtOAc) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.22 (2H, d, J=5.9 Hz), 3.94 (2H, s), 3.21 (2H, s), 2.41 (3H, s), 1.48 (9H, s).

Workup

customThe solvent was evaporated in vacuo
customthe residue partitioned between water and DCM
customthe solvent evaporated in vacuo
dissolutionThe residue was dissolved in CAN
filtrationThe suspension was filtered
customthe filtrate evaporated in vacuo
customThe residue was purified by flash chromatography (silica, iso-hexane/EtOAc)

Sources & evidence

ORD record: ord-07cf41eaf9d5453aba025d06bba2fc77
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802704B2

Reaction notes

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