Potassium Carbonate → HCID 178482360, compound

HRID 389462Notes

Reaction equation

[Cl:1][C:2]1[O:13][C:5]2=[C:6]([NH:11][CH3:12])[N:7]=[CH:8][C:9](I)=[C:4]2[CH:3]=1.[Si:14]([O:21][CH:22]1[CH2:27][CH2:26][CH:25]([N:28]2[CH:32]=[C:31](B3OC(C)(C)C(C)(C)O3)[CH:30]=[N:29]2)[CH2:24][CH2:23]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[Si:14]([O:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([N:28]2[CH:32]=[C:31]([C:9]3[CH:8]=[N:7][C:6]([NH:11][CH3:12])=[C:5]4[O:13][C:2]([Cl:1])=[CH:3][C:4]=34)[CH:30]=[N:29]2)[CH2:24][CH2:23]1)([C:17]([CH3:20])([CH3:18])[CH3:19])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 2-chloro-4-iodo-N-methylfuro[2,3-c]pyridin-7-amine (34.0 mg, 0.110 mmol), 1-[4-(tert-butyldimethylsilanyloxy)-cyclohexyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (55.1 mg, 0.136 mmol), (1,1′-bis-(diphenylphosphino)-ferrocene)palladium dichloride (8.6 mg, 0.012 mmol), and potassium carbonate (41.4 mg, 0.300 mmol) in 1,4-dioxane (2.3 mL) and water (0.9 mL) was irradiated under microwave heating at 85° C. for 30 min. Purification by ISCO chromatography (20 to 50% ethyl acetate:heptane) afforded 42.6 mg (82%) of the title compound as a light brown solid. 1H NMR (400 MHz, DMSO-d6): δ 8.15 (s, 1H), 8.07 (s, 1H), 7.84 (s, 1H), 7.36 (s, 1H), 6.88 (q, J=4.55 Hz, 1H), 4.17 (tt, J=3.85, 11.31 Hz, 1H), 3.73 (tt, J=4.01, 10.52 Hz, 1H), 2.91 (d, J=4.55 Hz, 3H), 1.99-2.10 (m, 2H), 1.82-1.97 (m, 4H), 1.38-1.53 (m, 2H), 0.88 (s, 9H), 0.08 (s, 6H); MS (ESI): 461.31, 463.30 [M+H]+; HPLC tR=4.28 min (ZQ3, nonpolar—5 min).

Workup

customwas irradiated under microwave
customPurification by ISCO chromatography (20 to 50% ethyl acetate:heptane)

Sources & evidence

ORD record: ord-d315db1271954c9c949a58ea3d3dc506
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378104B2

Reaction notes

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