Azobisisobutyronitrile → HCID 68104457, compound

HRID 509548Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]2[O:26][N:25]=[C:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)[CH:23]=2)=[CH:20][C:19]([C:34]2[CH:39]=[CH:38][C:37]([S:40]([CH:43]([CH3:45])[CH3:44])(=[O:42])=[O:41])=[CH:36][N:35]=2)=[CH:18][N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:53])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>CCOC(C)=O>[Br:53][CH2:33][C:30]1[CH:31]=[CH:32][C:27]([C:24]2[CH:23]=[C:22]([C:21]3[C:16]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[N:17][CH:18]=[C:19]([C:34]4[CH:39]=[CH:38][C:37]([S:40]([CH:43]([CH3:45])[CH3:44])(=[O:41])=[O:42])=[CH:36][N:35]=4)[CH:20]=3)[O:26][N:25]=2)=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 85 °C

Procedure

tert-Butyl N-tert-butoxycarbonyl-N-[5-(5-isopropylsulfonyl-2-pyridyl)-3-[3-(p-tolyl)isoxazol-5-yl]-2-pyridyl]carbamate (245 mg, 0.3860 mmol) was suspended in EtOAc (2.5 mL) followed by the addition of NBS (89.31 mg, 0.5018 mmol) and AIBN (6.338 mg, 0.03860 mmol). The mixture was heated to 85° C. and placed under a bright lamp for 2 hours. The reaction mixture was cooled to ambient temperature and washed with saturated aqueous NaHCO3/brine (1:1, ×2), dried (MgSO4), filtered and concentrated in vacuo to give the impure sub-title compound as a pale brown foam. This was used in the next step without any further purification.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
washwashed with saturated aqueous NaHCO3/brine (1:1, ×2)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0d4146b4d75c4a51ba9a6aea68af58fd
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096584B2

Reaction notes

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