1,2-Dimethoxyethane → HCID 118094038, compound

HRID 515542Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([S:12]([NH:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:14])=[O:13])[C:5]2[N:6]=[CH:7][CH:8]=[N:9][C:10]=2[CH:11]=1.[CH3:21][C:22]1[C:26](B2OC(C)(C)C(C)(C)O2)=[C:25]([CH3:36])[O:24][N:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(COC)OC>O>[CH:16]1([NH:15][S:12]([C:4]2[C:5]3[N:6]=[CH:7][CH:8]=[N:9][C:10]=3[CH:11]=[C:2]([C:26]3[C:22]([CH3:21])=[N:23][O:24][C:25]=3[CH3:36])[CH:3]=2)(=[O:14])=[O:13])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 7-chloro-N-cyclopentylquinoxaline-5-sulfonamide (0.07 g, 0.22 mmol), 3,5-dimethylisoxazole-4-boronic acid pinacol ester (0.15 g, 0.66 mM, Aldrich catalogue number 643882), Peppsi-iPr (0.014 g, 0.022 mM, Aldrich catalogue number 669032) and cesium carbonate (0.143 g, 0.44 mM) under nitrogen was added dimethoxyethane (3 mL) and water (1 mL). The reaction mixture was heated to 90° C. for 1 hour. The mixture is partitioned between water and ethyl acetate, the aqueous phase is discarded and the products are purified by silica gel (rf=0.36 in 1:1 hexanes/ethyl acetate) to give N-cyclopentyl-7-(3,5-dimethylisoxazol-4-yl)quinoxaline-5-sulfonamide as an off-white solid.

Workup

customThe mixture is partitioned between water and ethyl acetate
customthe products are purified by silica gel (rf=0.36 in 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-564eb76662db48d692942039d46f9036
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108953B2

Reaction notes

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