Dichloromethane → HCID 71114472, compound

HRID 710105Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.FC(F)(F)S(O[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=1)(=O)=O.[F-].[K+].C(Cl)Cl>CN(C=O)C>[NH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([C:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=3)=[CH:11][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

5-Bromobenzo[d]oxazol-2-amine (824 mg, 3.9 mmol) and tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (1.8 g, 5.8 mmol), Potassium fluoride (674 mg, 11.61 mmol) were dissolved in DMF under N2 atmosphere. This mixture was purged with N2 for 30 mins Pd(dppf)2Cl2.CH2Cl2 (252 mg, 0.3 mmol) was added to the above mixture and again purged with N2 for 30 mins. The reaction mixture was stirred at 90° C. for 12 h. Work up (EtOAc/H2O) followed by column purification on combiflash using a gradient mixture of EtOAc and Petether (1:1) as eluent afforded the titled compound (550 mg) as an off-white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.38-7.36 (m, 2H), 7.26-7.22 (m, 2H), 7.02 (d, J 7.9, 1H), 6.05 (s, 1H), 4.01-3.90 (m, 2H), 3.49-3.55 (m, 2H), 2.50-2.40 (m, 2H), 1.50 (s, 9H).

Workup

customThis mixture was purged with N2 for 30 mins Pd(dppf)2Cl2
customagain purged with N2 for 30 mins
customfollowed by column purification on combiflash
additiona gradient mixture of EtOAc and Petether (1:1) as eluent

Sources & evidence

ORD record: ord-c6854bdcabee4fec9e6f49aa3eb595bb
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181214B2

Reaction notes

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