Dimethyl Sulfoxide → HCID 67109260, compound

HRID 2370985Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[C:18]2[C:19]([CH3:24])=[N:20][O:21][C:22]=2[CH3:23])=[CH:5][CH:4]=1.O(C1C=CC(C(C2C=CC(OC#N)=CC=2)(C)C)=CC=1)[C:26]#[N:27].CS(C)=O.CCN(CC)CC>[Cl-].[Na+].O>[CH3:24][C:19]1[C:18]([C:10]2[N:11]([C:26]#[N:27])[C:12]3[C:17]([C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:22]([CH3:23])[O:21][N:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

4-(3-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole (37 mg, 0.12 mmol) and 2,2-bis-(4-cyanatophenyl)propane (0.6 eq) were mixed in a vial. 1.8 ml DMSO and Et3N (3 eq) were added and the mixture was heated at 120° C. in microwave. 2,2-bis-(4-cyanatophenyl)propane (5.7 eq) and Et3N (40 eq) were added and the mixture was heated at 150° C. for 25 min in microwave. Brine was added and the aqueous layer was extracted with EtOAc 6×. The combined organic layers were dried over Na2SO4 and concentrated. The crude product was taken up in DCM, filtered through cotton wool and purified on silica (EtOAc/n-Heptane 1:9-2:8). 25.7 mg 2-(3,5-dimethylisoxazol-4-yl)-3-(4-methoxyphenyl)-1H-indole-1-carbonitrile was obtained as a yellowish solid.

Workup

temperaturethe mixture was heated at 150° C. for 25 min in microwave
extractionthe aqueous layer was extracted with EtOAc 6×
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated
filtrationfiltered through cotton wool
custompurified on silica (EtOAc/n-Heptane 1:9-2:8)

Sources & evidence

ORD record: ord-b736c4db9ee244ebb38806e34fcf96bd
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710243B2

Reaction notes

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