Potassium Carbonate → HCID 86720792, compound

HRID 1776081Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([N:15]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)O1.Br[C:35]1[CH:40]=[N:39][C:38]([Br:41])=[CH:37][N:36]=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:41][C:38]1[N:39]=[CH:40][C:35]([C:9]2[CH:10]=[CH:11][C:12]([N:15]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)=[N:36][CH:37]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-(o-tolyl)naphthalen-1-amine (Compound 22) (0.55 g, 1.26 mmol), 2,5-dibromopyrazine (0.77 g, 3.0 mmol), Pd(PPh3)4 (0.1 g, 0.09 mmol), K2CO3 (0.414 g, 3 mmol) in dioxane/water (40 mL/8 mL) was degassed and heated at 80° C. overnight. The resulting mixture was worked up with ethyl acetate/brine, dried over Na2SO4, loaded on silica gel and purified by flash column using eluents of hexanes/dichloromethane 9:1 to 3:2. After removal of solvents, a yellow solid (Compound 23) was obtained, 0.44 g in 75% yield.

Workup

customwas degassed
dry with materialdried over Na2SO4
custompurified by flash column
customAfter removal of solvents

Sources & evidence

ORD record: ord-cbc11b31de844502b8e5ba3cd336c000
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09263681B2

Reaction notes

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