Pyridine → HCID 66744369, compound

HRID 1959445Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([C:23]2[O:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:26][N:27]=2)[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.N1C=CC=[CH:36][CH:35]=1.C(B1OB(C=C)OB(C=C)O1)=C.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]([O:10][C:9]([N:8]([C:5]1[C:4]([C:23]2[O:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:26][N:27]=2)=[N:3][C:2]([CH:35]=[CH2:36])=[CH:7][N:6]=1)[C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (500 mg, 0.96 mmol) in toluene (2 mL) and ethanol (2 mL) was added pyridine; 2,4,6-trivinyl-1,3,5,2,4,6-trioxatriborinane (290 mg, 1.2 mmol), K2CO3 (533 mg, 4 mmol) and Pd(PPh3)4 (112 mg, 0.1 mmol). The reaction mixture was heated at 60° C. under an atmosphere of nitrogen for 1 h. The reaction mixture was filtered, concentrated and the crude material obtained was purified via silica gel column chromatography using EtOAc/hex gradient to obtain tert-butyl N-tert-butoxycarbonyl-N-[3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-vinyl-pyrazin-2-yl]carbamate (449 mg, 100%).

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated
customthe crude material obtained
customwas purified via silica gel column chromatography

Sources & evidence

ORD record: ord-f5a5ce26de2b432bb036c0239f3f465a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410112B2

Reaction notes

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