Morpholine → HCID 86592036, compound

HRID 1349551Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C@@H:7]([CH3:21])[CH2:6][C@H:5]2[N:22]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:23](=[O:26])[CH2:24][CH3:25].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.CC(C)([O-])C.[Na+].[NH:86]1[CH2:91][CH2:90][O:89][CH2:88][CH2:87]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]>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([N:22]([C@H:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([N:86]4[CH2:91][CH2:90][O:89][CH2:88][CH2:87]4)[CH:3]=3)[N:8]([C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C@@H:7]([CH3:21])[CH2:6]2)[C:23](=[O:26])[CH2:24][CH3:25])=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(±)-Cis-N-[6-bromo-1-(4-fluoro-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-chloro-phenyl)-propionamide was dissolved in toluene, followed by Pd2(dba)3, BINAP, sodium tert-butoxide, and morpholine. The reaction mixture was heated to 90° C. for 24 hours. The reaction mixture was cooled to room temperature and filtered through Celite® and concentrated. Crude mixture was purified by flash chromatography on silica gel using a gradient elution of hexane-ethylacetate (10–50%).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through Celite®
concentrationconcentrated
customCrude mixture was purified by flash chromatography on silica gel using
washa gradient elution of hexane-ethylacetate (10–50%)

Sources & evidence

ORD record: ord-6aa1290a13e240a797dcbf3527a8ffde
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211672B2

Reaction notes

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