1,4-Dioxane → HCID 86658473, compound

HRID 335864Notes

Reaction equation

HRID 335864 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[O:8][C:9]3[C:10]([C:17]4([CH2:21][O:20][C:19]([NH2:22])=[N:18]4)[C:4]=2[CH:3]=1)=[N:11][C:12]([Cl:16])=[CH:13][C:14]=3[F:15].[F:23][C:24]1[C:29](B(O)O)=[CH:28][CH:27]=[CH:26][N:25]=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>[Cl:16][C:12]1[N:11]=[C:10]2[C:17]3([C:4]4[CH:3]=[C:2]([C:29]5[C:24]([F:23])=[N:25][CH:26]=[CH:27][CH:28]=5)[CH:7]=[CH:6][C:5]=4[O:8][C:9]2=[C:14]([F:15])[CH:13]=1)[CH2:21][O:20][C:19]([NH2:22])=[N:18]3

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 27832702-Fluoropyridine-3-boronic acidHCID 86658474HCID 86658474, compound

Product 1

HCID 86658473HCID 86658473, compound

Reagents, catalysts & solvents 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 8-bromo-2-chloro-4-fluoro-5′H-spiro[chromeno[3,2-b]pyridine-10,4′-oxazol]-2′-amine (27.0 mg, 0.070 mmol), bis-(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(ii) (2.486 mg, 3.51 μmol), 2-fluoropyridine-3-boronic acid (10.8 mg, 0.077 mmol) and potassium phosphate (29.8 mg, 0.140 mmol) in a 2:1 mixture of dioxane and water (1.2 mL) was heated at 105° C. in the microwave for 35 min. The reaction mixture was purified by column chromatography (SiO2, CH2Cl2 to CH2Cl2/EA=2:1 to 1:1 to 3:4 to 1:2 to 1:3 to pure EA) to give 2-chloro-4-fluoro-8-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[3,2-b]pyridine-10,4′-oxazol]-2′-amine as an off white solid.

Workup

  1. customThe reaction mixture was purified by column chromatography (SiO2, CH2Cl2 to CH2Cl2/EA=2:1 to 1:1 to 3:4 to 1:2 to 1:3 to pure EA)

Sources & evidence

ORD record
ord-7c7eca81e0324b168db4bbc84df8288b
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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