Morpholine → HCID 11532501, compound

HRID 2104189Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH3:18])[C:12]([C:19]([CH:21]1[CH2:23][CH2:22]1)=[O:20])=[C:11]2[C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>CC(O)(C)C.CCCCCCC.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[CH:21]1([C:19]([C:12]2[C:13]([CH3:18])=[N:14][C:15]3[C:10]([C:11]=2[C:24]2[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=2)=[CH:9][C:8]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[CH:17][CH:16]=3)=[O:20])[CH2:22][CH2:23]1

Participants

Conditions

Temperature: 110 °C

Procedure

A tube placed under argon was charged with tris(dibenzylideneacetone)dipalladium chloroform complex (5 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (5 mg) and cesium carbonate (110 mg, 0.33 mmol). [6-Bromo-4-(4-methanesulfonyl-phenyl)-2-methyl-quinolin-3-yl]-cyclopropyl-methanone [example 50] (100 mg, 0.22 mmol) in t-BuOH (5 ml) was added, followed by morpholine (24 mg, 0.27 mmol). The tube was sealed and heated at 110° C. for 6 hrs. The reaction mixture was cooled to 20° C., diluted with heptane, and filtered through Celite and purified directly by flash chromatography on silica gel in heptane/AcOEt 80:20 to give a yellow solid (52 mg, 51%). MS: m/z=451 (M+H).

Workup

customA tube placed under argon
customThe tube was sealed
temperatureThe reaction mixture was cooled to 20° C.
filtrationfiltered through Celite
custompurified directly by flash chromatography on silica gel in heptane/AcOEt 80:20

Sources & evidence

ORD record: ord-7f80695696004d669266323d3073ffdf
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576217B2

Reaction notes

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