Potassium Carbonate → HCID 86720786, compound

HRID 1776073Notes

Reaction equation

[CH3:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[N:4]([C:12]1[CH:17]=[CH:16][C:15](B2OC(C)(C)C(C)(C)O2)=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11].Br[C:32]1[CH:37]=[N:36][C:35]([Br:38])=[CH:34][N:33]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C.[Cl-].[Na+].O>O1CCOCC1.O.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>[Br:38][C:35]1[N:36]=[CH:37][C:32]([C:15]2[CH:14]=[CH:13][C:12]([N:4]([C:3]3[CH:27]=[CH:28][CH:29]=[CH:30][C:2]=3[CH3:1])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[CH3:11])=[CH:17][CH:16]=2)=[N:33][CH:34]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-(o-tolyl)aniline (Compound 12) (3.3 g, 8.3 mmol), 2,5-dibromopyrazine (4.27 g, 16 mmol), Pd(PPh3)4 (0.46 g, 0.4 mmol), K2CO3 (2.21 g, 16 mmol) in dioxane/water (100 mL/16 mL), was degassed and heated at about 80° C. overnight. The resulting mixture was worked up with ethyl acetate/brine, dried over Na2SO4, loaded on silica gel, purified by flash column using eluents of hexanes to hexanes/dichloromethane 9:1 to 6:1 to 4:1). The desired fraction was collected, and a yellow solid (Compound 13) was obtained after removal of solvents (1.9 g, in 53% yield).

Workup

dry with materialdried over Na2SO4
custompurified by flash column
customThe desired fraction was collected

Sources & evidence

ORD record: ord-3cbed95112d44ec882a0b25e206f8ad7
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09263681B2

Reaction notes

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