Dichloromethane → HCID 86727194, compound

HRID 579373Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH2:13])=[N:10][N:9]=2)=[C:4]([Cl:14])[CH:3]=1.[NH:15]1[CH:19]=[C:18](B(O)O)[CH:17]=[N:16]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[Cl:14][C:4]1[CH:3]=[C:2]([C:18]2[CH:19]=[N:15][NH:16][CH:17]=2)[CH:7]=[CH:6][C:5]=1[C:8]1[S:12][C:11]([NH2:13])=[N:10][N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a microwave vial was added 5-(4-bromo-2-chlorophenyl)-1,3,4-thiadiazol-2-amine (500 mg, 1.721 mmol), 4-pyrazole boronic acid pinacle ester (668 mg, 3.44 mmol), cesium carbonate (1.68 g, 5.16 mmol), Pd2(dba)3.CH2Cl2 (178 mg, 0.172 mmol), and Xphos (82 mg, 0.172 mmol), followed by addition of 1,4-dioxane (2 mL)/H2O (0.5 mL). The vial was purged with N2 3 times and the reaction mixture was heated via microwave irradiation at 100° C. for 1 h. The reaction mixture was filtered through a disposable filter funnel, washed with EtOAc, concentrated in vacuo, and purified by silica gel chromotography (2% to 15% MeOH/DCM) to afford 5-(2-chloro-4-(1H-pyrazol-4-yl)phenyl)-1,3,4-thiadiazol-2-amine (250 mg, MS: 278.0 [M+H+].)

Workup

customThe vial was purged with N2 3 times
filtrationThe reaction mixture was filtered through a disposable filter funnel
washwashed with EtOAc
concentrationconcentrated in vacuo
custompurified by silica gel chromotography (2% to 15% MeOH/DCM)

Sources & evidence

ORD record: ord-dbff429a70734d428b8018f36734f236
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040712B2

Reaction notes

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