Potassium Carbonate → HCID 86648127, compound

HRID 2388233Notes

Reaction equation

[OH:1][C:2]1[C:3]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:4]=2[C:5]([I:13])=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].Cl[CH2:24][C:25]1[C:26]2[C:31]([CH:32]=[C:33]3[C:38]=1[CH:37]=[CH:36][CH:35]=[CH:34]3)=[CH:30][CH:29]=[CH:28][CH:27]=2.C1OCCOCCOCCOCCOCCOC1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.CN(C=O)C>[CH:27]1[C:26]2[C:31](=[CH:32][C:33]3[C:38]([C:25]=2[CH2:24][O:1][C:2]2[C:3]4[O:16][N:15]=[C:14]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)[C:4]=4[C:5]([I:13])=[N:6][C:7]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Ethyl 7-hydroxy-4-iodo-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (300 mg, 0.73 mmol), 9-chloromethylanthracene (249 mg, 1.10 mmol), 18-crown-6 (29 mg, 0.11 mmol) and K2CO3 (152 mg, 1.10 mmol) were added to DMF, and the mixture was stirred at 55° C. for 3 h. EtOAc (50 mL) was added and the organic layer was washed with brine and dried over MgSO4. Solvent was removed in vacuo and the crude product was purified twice by flash chromatography (0-30% EtOAc/hexanes) to give 200 mg of the title compound. 1H NMR (CDCl3, 200 MHz): δ=8.65-8.80 (m, 2H), 8.18 (s, 1H), 7.70-7.80 (m, 2H), 7.40-7.55 (m, 3H), 7.18-7.30 (m, 6H), 6.30 (s, 2H), 3.95 (q, 2H, J=7.0 Hz), 0.72 (t, 3H, J=7.2 Hz).

Workup

washthe organic layer was washed with brine
dry with materialdried over MgSO4
customSolvent was removed in vacuo
customthe crude product was purified twice by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-c007cca76dfc4cfbb03cef3fd789332b
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08269008B2

Reaction notes

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