Potassium Carbonate → HCID 16124643, compound

HRID 1642509Notes

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

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, 1 H) 8.10 (d, J=7.84 Hz, 1 H) 7.67 (m, 2 H), 7.60 (m, 5 H) 7.27 (m, 2 H). [M+H] calc'd for C17H12N2, 245; found 245.

Workup

customPurification by HPLC

Sources & evidence

ORD record: ord-4f8216d7b58e48629680810379789c6e
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119655B2

Reaction notes

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