Nitrogen → 6-(o-Tolyl)-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One

HRID 897210Notes

Reaction equation

N#N.Br[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:18][CH2:17]1.C([O-])([O-])=O.[Cs+].[Cs+].[C:37]1([CH3:46])[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1OBO>COCCOC.O.CCO>[C:37]1([CH3:46])[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH:23]=[CH:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 160 °C

Procedure

Into a dry microwave vial under N2 was added 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(PPh3)Cl2 (˜1 mol %), and Cs2CO3 (17.8 mg, 0.0547 mmol) in DME/H2O/EtOH (7/3/2, 0.5 mL). O-tolyl boronic acid (6.3 mg, 0.046 mmol) was added and the solution was heated in the microwave for 5 minutes at 160° C., filtered, and was purified by Prep HPLC to give 6 mg (23%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 451 (M−H)+; 1H NMR (300 MHz, DMSO) δ ppm 1.78-1.86 (m, 2H), 2.19 (br d, 2H), 2.22 (s, 3H), 3.13-3.19 (m, 2H), 3.58 (br d, 2H), 3.81-3.92 (m, 3H), 5.43 (s, 1H), 6.34-6.40 (m, 1H), 6.88 (d, 1H), 7.23-7.43 (m. 10H), 7.54 (m, 2H), 8.14 (d, 1H).

Workup

filtrationfiltered
customwas purified by Prep HPLC

Sources & evidence

ORD record: ord-6162aca7d27e4ae19e8488eeef4845ab
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921821B2

Reaction notes

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