Potassium Carbonate → HCID 86725107, compound

HRID 634184Notes

Reaction equation

Br[C:2]1[O:3][C:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:11]=[C:10]3[C:26]2[CH:31]=[N:30][CH:29]=[C:28]([CH:32]3[CH2:34][CH2:33]3)[N:27]=2)=[N:5][N:6]=1.[NH:35]1[CH:39]=[CH:38][C:37](B(O)O)=[N:36]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:32]1([C:28]2[N:27]=[C:26]([C:10]3[C:9]4[C:13](=[CH:14][CH:15]=[C:7]([C:4]5[O:3][C:2]([C:37]6[NH:36][N:35]=[CH:39][CH:38]=6)=[N:6][N:5]=5)[CH:8]=4)[N:12]([S:16]([C:19]4[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=4)(=[O:18])=[O:17])[CH:11]=3)[CH:31]=[N:30][CH:29]=2)[CH2:34][CH2:33]1

Participants

Conditions

Temperature: 100 °C

Procedure

A brown mixture of 2-bromo-5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazole (48.4 mg, 0.090 mmol), 1H-pyrazol-3-ylboronic acid (J&W Pharmlab, LLC, Levittown, Pa.; 30.3 mg, 0.271 mmol), Pd(PPh3)4 (20.85 mg, 0.018 mmol), and potassium carbonate (37.4 mg, 0.271 mmol) in a mixture of dioxane (1.0 mL) and H2O (0.250 mL) was stirred under argon at 100° C. for 1.5 h. The mixture was cooled to RT, concentrated onto silica gel, and purified chromatographically (silica gel, 0-100% (10% MeOH-EtOAc)/Hex) to provide 2-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-5-(1H-pyrazol-5-yl)-1,3,4-oxadiazole (19.6 mg, 0.037 mmol, 42%) as a light-yellow solid: MS (ESI, pos. ion) m/z: 524.2 (M+1).

Workup

temperatureThe mixture was cooled to RT
concentrationconcentrated onto silica gel
custompurified chromatographically (silica gel, 0-100% (10% MeOH-EtOAc)/Hex)

Sources & evidence

ORD record: ord-63e3e111f3434692a662537d97377d8e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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