Quinoline → 34500-40-8

HRID 1618477Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=CC=CC=2)[CH2:3][CH2:2]1.[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-:21].[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>O1CCOCC1.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]>[O:21]1[CH2:4][CH2:9][N:1]([C:11]2[CH:12]=[CH:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:10]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of indoline (1 eq), quinoline (2 eq), cesium carbonate (2 eq), Pd2(dba)3 (0.1 eq) and (±) BINAP (0.15 eq) were dissolved in 1,4-dioxane (0.4M). The resulting mixture was purged with argon and subjected to microwave heating at 140° C. for 3 h. The crude residue was purified by chromatography to give the desired morpholino-quinoline product.

Workup

customThe resulting mixture was purged with argon
customThe crude residue was purified by chromatography

Sources & evidence

ORD record: ord-40aceeab2af24e50952e65f0770eeae2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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