Potassium Carbonate → HCID 86720785, compound

HRID 1776069Notes

Reaction equation

[C:1]1([N:7]([C:18]2[CH:23]=[CH:22][C:21](B3OC(C)(C)C(C)(C)O3)=[CH:20][CH:19]=2)[C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:34]1[CH:39]=[N:38][C:37]([Br:40])=[CH:36][N:35]=1.C([O-])([O-])=O.[K+].[K+]>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:40][C:37]1[N:38]=[CH:39][C:34]([C:4]2[CH:3]=[CH:2][C:1]([N:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:8]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:5]=2)=[N:35][CH:36]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)naphthalen-1-amine (Compound 7) (2.91 g, 6.91 mmol), 2,5-dibromopyrazine (3.56 g, 13.8 mmol), Pd(PPh3)4 (0.346 g, 0.3 mmol), K2CO3 (1.93 g, 14 mmol) in dioxane/water (80 mL/15 mL), was degassed and heated at about 85° C. overnight. The resulting mixture was diluted with ethyl acetate (250 mL), washed with brine, dried over Na2SO4, loaded on silica gel and purified by flash column using eluents of hexanes to hexanes/dichloromethane 4:1 to 2:1 to 3:2). The desired fraction was collected, after removal of solvent to give a yellow solid (Compound 8) (2.2 g, in 70.4% yield).

Workup

customwas degassed
additionThe resulting mixture was diluted with ethyl acetate (250 mL)
washwashed with brine
dry with materialdried over Na2SO4
custompurified by flash column
customThe desired fraction was collected
customafter removal of solvent

Sources & evidence

ORD record: ord-a845c9695eb740fb9a427f605d361fb1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09263681B2

Reaction notes

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