Potassium Carbonate → HCID 16124643, compound

HRID 1882199Notes

Reaction equation

HRID 1882199 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1[CH:14]=[CH:13][CH:12]=[N:11][C:5]=1[NH:6]2.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[C:15]1([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[C:4]2[CH:14]=[CH:13][CH:12]=[N:11][C:5]=2[NH:6]3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 16124640HCID 16124640, compound

Product 1

HCID 16124643HCID 16124643, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

Compound 4 (20 mg, 0.081 mmol) was mixed with phenylboronic acid (20 mg, 0.16 mmol) and Tetrakis Pd(0) catalyst (19 mg, 0.016 mmol) in a solution comprising dioxane (3 ml) and a saturated K2CO3 solution (1 ml). The mixture was heated in a microwave reactor at 150° C. for 20 minutes. Purification by HPLC afforded the title compound as a tan solid (4 mg, 22%). 1H NMR (400 MHz, CD3OD) δ 8.39 (s, 1H) 8.10 (d, J=7.84 Hz, 1H) 7.67 (m, 2H) 7.60 (m, 5H) 7.27 (m, 2H). [M+H] calc'd for C17H12N2, 245; found 245.

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-75ae9c47083f4a40a95797655d0fe914
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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