Cesium carbonate → HCID 16667230, compound

HRID 1927599Notes

Reaction equation

Br[C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][C:10]2[C:11]([CH3:16])=[N:12][O:13][C:14]=2[CH3:15])=[O:7])=[CH:4][C:3]=1[F:19].[CH2:20]([N:22]([CH2:38][CH3:39])[C:23](=[O:37])[CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[CH3:21].C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:38]([N:22]([CH2:20][CH3:21])[C:23]([CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[N:25]1[CH2:26][CH2:27][N:28]([C:2]2[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][C:10]3[C:11]([CH3:16])=[N:12][O:13][C:14]=3[CH3:15])=[O:7])=[CH:4][C:3]=2[F:19])[CH2:29][CH2:30]1)=[O:37])[CH3:39]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromo-N-(3,5-dimethyl-isoxazol-4-ylmethyl)-3-fluoro-benzamide (0.31 mmol), N,N-diethyl-2-phenyl-2-piperazin-1-yl-acetamide (0.20 mmol), Cs2CO3 (1.2 mmol), Pd2(dba)3 (0.0030 mmol), and BINAP (0.0120 mmol) in toluene (2.0 mL) was stirred at 100° C. for 16 h. The mixture was cooled to rt and purified by PTLC to provide the title compound (60 mg, 58%). MS (ESI): mass calcd. for C29H36FN5O3, 521.28. m/z found, 522.4 [M+H]+. 1H NMR (CDCl3): 7.50-7.25 (m, 7H), 6.82 (t, J=8.5, 1H), 6.51 (t, J=5.2, 1H), 4.31 (d, J=5.3, 2H), 4.22 (s, 1H), 3.48-3.36 (m, 2H), 3.30-3.10 (m, 6H), 2.73-2.60 (m, 4H), 2.36 (s, 3H), 2.21 (s, 3H), 1.12-1.02 (m, 6H).

Workup

temperatureThe mixture was cooled to rt
custompurified by PTLC

Sources & evidence

ORD record: ord-3ddf56ab7fb44d0b8329377dd9565648
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183239B2

Reaction notes

Loading…