Potassium Carbonate → HCID 86712052, compound

HRID 1755524Notes

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.I[C:34]1[CH:39]=[CH: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[CH: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: 95 °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 29) (2.32 g, 5.51 mmol), 2-iodo-5-bromo-pyridine (3.13 g, 11 mmol), Pd(PPh3)4 (0.346 g, 0.3 mmol) and K2CO3 (1.38 g, 10 mmol) in dioxane/water (60 mL/10 mL) was degassed and heated at about 95° C. overnight. The resulting mixture was mixed with ethyl acetate/brine, dried over Na2SO4, loaded on silica gel, and purified by flash column (hexanes to hexanes/dichloromethane 9:1 to 3:1). The desired fraction was collected and a light yellow solid (Compound 30) was obtained after removal of solvents (2.17 g, in 87% yield).

Workup

customwas degassed
additionThe resulting mixture was mixed with ethyl acetate/brine
dry with materialdried over Na2SO4
custompurified by flash column (hexanes to hexanes/dichloromethane 9:1 to 3:1)
customThe desired fraction was collected

Sources & evidence

ORD record: ord-e6709aadac344561aece592857c0e8fb
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09172051B2

Reaction notes

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