Potassium Carbonate → HCID 68282946, compound

HRID 1855308Notes

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:43])=[CH:25][C:26]([O:41][CH3:42])=[CH:27][C:28]=3[C:29]32[C:35]2=[N:36][CH2:37][CH2:38][CH2:39][N:34]2[C:33]([NH2:40])=[N:32]3)=[CH:20][CH:19]=1>O1CCOCC1.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>[F:43][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][CH2:37][CH2:38][CH2:39][N:34]4[C:33]([NH2:40])=[N:32]3)[C:28]=2[CH:27]=[C:26]([O:41][CH3:42])[CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium carbonate (1M aq. Solution) (1.391 mL, 1.391 mmol), 2-fluoropyridin-3-ylboronic acid (98 mg, 0.696 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phospine)dichloropalladium(II) (0.34 mmol) and 7′-bromo-4′-fluoro-2′-methoxy-3,4-dihydro-2H-spiro[imidazo[1,5-a]pyrimidine-8,9′-xanthen]-6-amine (150 mg, 0.348 mmol) were combined in dioxane (3 mL), capped under argon, and heated at 100° C. for 2 hours. The solution was concentrated, and the product was purified from the crude concentrate via silica gel column chromatography (RediSep 12 g column) using 0-100% 90/10/1 (DCM/MeOH/ammonia) in DCM to afford 4′-fluoro-7′-(2-fluoropyridin-3-yl)-2′-methoxy-3,4-dihydro-2H-spiro[imidazo[1,5-a]pyrimidine-8,9′-xanthen]-6-amine (30 nig, 0.067 mmol). MS m/z=449.2 [M+H].

Workup

customcapped under argon
concentrationThe solution was concentrated
customthe product was purified from the crude
concentrationconcentrate via silica gel column chromatography (RediSep 12 g column)

Sources & evidence

ORD record: ord-06cbf8de040646fc8c690de7c84f563a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962859B2

Reaction notes

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