4,7-Dichloroquinoline → HCID 70944812, compound

HRID 1190896Notes

Reaction equation

[N:1]1([C:7]2[CH:8]=[C:9]([CH:11]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:13]=2)[NH2:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=2)[N:24]=[CH:23][CH:22]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>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].O1CCOCC1>[N:1]1([C:7]2[CH:8]=[C:9]([NH:10][C:21]3[C:30]4[C:25](=[CH:26][C:27]([Cl:31])=[CH:28][CH:29]=4)[N:24]=[CH:23][CH:22]=3)[CH:11]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[CH:13]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 90 °C

Procedure

In a oven-dried flask and under a nitrogen atmosphere, were placed 3,5-bis(morpholin-4-yl)aniline (63 mg, 0.22 mmol), 4,7-dichloroquinoline (43 mg, 1 eq), (+/−) BINAP (7 mg, 0.1 eq), Cs2CO3 (99 mg, 1.4 eq), Pd2dba3 (5 mg, 0.02 eq) and 2 mL of dry 1,4-dioxane. The mixture was stirred at 90° C. for 24 h. The solution was filtered through a celite pad and evaporated. The residue was purified by preparative thin-layer chromatography (DCM/MeOH//95/5) to yield expected compound as a yellow solid (27 mg, 29% yield). m/z (ESI) 425.3 [M+H]+;

Workup

customIn a oven-dried flask and under a nitrogen atmosphere, were placed
filtrationThe solution was filtered through a celite pad
customevaporated
customThe residue was purified by preparative thin-layer chromatography (DCM/MeOH//95/5)

Sources & evidence

ORD record: ord-d18a400961f74826a7d37c0317c6a1b8
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680095B2

Reaction notes

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