1,4-Dioxane → HCID 58466244, compound

HRID 335865Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]2[C:8]3([C:14]4[CH:15]=[C:16]([C:21]5[C:22]([F:27])=[N:23][CH:24]=[CH:25][CH:26]=5)[CH:17]=[CH:18][C:19]=4[O:20][C:5]2=[C:4]([F:28])[CH:3]=1)[CH2:12][O:11][C:10]([NH2:13])=[N:9]3.[O:29]1[CH2:34][CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH2:31][CH2:30]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].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.O>[O:29]1[CH2:30][CH:31]=[C:32]([C:2]2[N:7]=[C:6]3[C:8]4([C:14]5[CH:15]=[C:16]([C:21]6[C:22]([F:27])=[N:23][CH:24]=[CH:25][CH:26]=6)[CH:17]=[CH:18][C:19]=5[O:20][C:5]3=[C:4]([F:28])[CH:3]=2)[CH2:12][O:11][C:10]([NH2:13])=[N:9]4)[CH2:33][CH2:34]1

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of 2-chloro-4-fluoro-8-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[3,2-b]pyridine-10,4′-oxazol]-2′-amine (19.00 mg, 0.047 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (24.90 mg, 0.119 mmol), bis-(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(ii) (1.678 mg, 2.370 μmol) and potassium phosphate (22.14 mg, 0.104 mmol) in a 2:1 mixture of dioxane and water (1.5 mL was heated at 135° C. in the microwave for 25 minutes. The reaction mixture was purified by column chromatography (SiO2, CH2Cl2 to CH2Cl2/EA=3:1 to 2:1 to 1:1 to pure EA to EA/MeOH=100:5) to give 2-(3,6-dihydro-2H-pyran-4-yl)-4-fluoro-8-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[3,2-b]pyridine-10,4′-oxazol]-2′-amine as a off white solid.

Workup

customThe reaction mixture was purified by column chromatography (SiO2, CH2Cl2 to CH2Cl2/EA=3:1 to 2:1 to 1:1 to pure EA to EA/MeOH=100:5)

Sources & evidence

ORD record: ord-c2fabb4504b54adaad291b76bddb06a6
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883782B2

Reaction notes

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