Sodium Iodide → HCID 68535459, compound

HRID 2389324Notes

Reaction equation

CS([O:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[CH:12]=[CH:11][C:10]([CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:9]1)(=O)=O.O[C:29]1[CH:30]=[C:31]([CH:41]=[CH:42][CH:43]=1)[O:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37].C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>CCOC(C)=O.CN(C=O)C>[C:16]1([CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]2[CH:11]=[CH:12][C:13](=[O:14])[N:8]([CH2:7][CH2:6][O:5][C:29]3[CH:30]=[C:31]([CH:41]=[CH:42][CH:43]=3)[O:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[N:9]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-[3-(diphenylmethyl)-6-oxopyridazin-1(6H)-yl]ethyl methanesulfonate (200 mg), ethyl 4-(3-hydroxyphenoxy)butanoate (140 mg), K2CO3 (93 mg), sodium iodide (94 mg), and DMF (2 mL) was stirred at 80° C. for 2 hours. After cooling, the reaction mixture was diluted with EtOAc (50 mL) and washed with water (30 mL) and brine (30 mL) two times. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to give crude oil. The crude oil was purified by silica gel column chromatography (n-hexane:EtOAc=1:1) to give ethyl 4-(3-{2-[3-(diphenylmethyl)-6-oxopyridazin-1(6H)-yl]ethoxy}phenoxy)butanoate (87 mg) as a pale yellow oil.

Workup

temperatureAfter cooling
washwashed with water (30 mL) and brine (30 mL) two times
dry with materialThe organic layer was dried over anhydrous MgSO4
filtrationfiltered
customevaporated in vacuo
customto give crude oil
customThe crude oil was purified by silica gel column chromatography (n-hexane:EtOAc=1:1)

Sources & evidence

ORD record: ord-5049dbab1632412f9a7a9d7c30b186be
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273745B2

Reaction notes

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