Sodium Iodide → 6-Methoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile

HRID 499129Notes

Reaction equation

ClCCO[C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:31][CH3:32].N1(C2CCNCC2)CCCCC1.[I-].[Na+]>COCCOC>[CH3:32][O:31][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:5]=1)[N:12]=[CH:11][C:10]([C:15]#[N:16])=[C:9]2[NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 137.5 °C

Procedure

A mixture of 222.5 mg (0.5 mmol) of 7-(2-chloroethoxy)-6-methoxy-4-(4-phenoxyphenylamino)quinolin-3-carbonitrile, 841.4 mg (5.0 mmol) of 4-piperidinopiperidine and 49.5 mg (0.33 mmol) of sodium iodide in 6.0 mL of ethylene glycol dimethyl ether are heated in a sealed tube at 135-140° C. for 17 hours to yield the crude product. Solvents are removed in vacuo. Purification of the oily residue is carried out by preparative thin layer chromatography (eluting with 85:15 dichloromethane/methanol) to provide 137.7 mg of 742-[1,4′]bipiperidinyl-1′-yl-ethoxy)-6-methoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile as a light yellow solid, mp 141° C. (decompose).

Workup

customto yield the crude product
customSolvents are removed in vacuo
customPurification of the oily residue
washis carried out by preparative thin layer chromatography (eluting with 85:15 dichloromethane/methanol)

Sources & evidence

ORD record: ord-13f62102872e4733b5775679d884d5b8
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767671B2

Reaction notes

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