Potassium Carbonate → HCID 60164215, compound

HRID 1855301Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[C:13](B(O)O)=[CH:12][CH:11]=[CH:10][N:9]=1.Br[C:18]1[CH:31]=[C:30]2[C:21]([O:22][C:23]3[C:24]([F:42])=[CH:25][C:26]([O:40][CH3:41])=[CH:27][C:28]=3[C:29]32[C:35]2=[N:36][CH:37]=[CH:38][N:34]2[C:33]([NH2:39])=[N:32]3)=[CH:20][CH:19]=1>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl.O1CCOCC1>[F:42][C:24]1[C:23]2[O:22][C:21]3[C:30](=[CH:31][C:18]([C:13]4[C:8]([F:7])=[N:9][CH:10]=[CH:11][CH:12]=4)=[CH:19][CH:20]=3)[C:29]3([C:35]4=[N:36][CH:37]=[CH:38][N:34]4[C:33]([NH2:39])=[N:32]3)[C:28]=2[CH:27]=[C:26]([O:40][CH3:41])[CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A pressure vessel was charged with potassium carbonate (1M solution) (49 mL, 49 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phospine)dichloropalladium(II) (1.739 g, 2.457 mmol), 2-fluoropyridin-3-ylboronic acid (3.46 g, 24.57 mmol), and 7′-bromo-4′-fluoro-2′-methoxyspiro[imidazo[1,5-a]imidazole-7,9′-xanthen]-5-amine (5.1 g, 12.28 mmol). Dioxane (150 mL) was added and the mixture was capped under argon, sonicated for 1 min and heated at 100° C. for 4 hours. The solution was concentrated. Material was purified via silica gel column chromatography using 50-100% ethyl acetate in hexane to afford 4′-fluoro-7′-(2-fluoropyridin-3-yl)-2′-methoxyspiro[imidazo[1,5-a]imidazole-7,9′-xanthen]-5-amine (3 g, 6.95 mmol) as a white solid.

Workup

customthe mixture was capped under argon
customsonicated for 1 min
concentrationThe solution was concentrated
customMaterial was purified via silica gel column chromatography

Sources & evidence

ORD record: ord-8b2c4d6f00f0472aafc2c7b83cc7935c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962859B2

Reaction notes

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