2-Bromopyridine → HCID 66609728, compound

HRID 75709Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH2:13])=[N:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15].Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15]

Participants

Conditions

Temperature: 120 °C

Procedure

7-methoxy-6-nitroquinazolin-4-ylamine (300 mg, 1.36 mmol) in <Step 6> of Example 23, 2-bromopyridine (0.2 mL, 2.04 mmol), palladium acetate (31 mg, 0.136 mmol), Xantphos (158 mg, 0.273 mmol) and cesium carbonate (888 mg, 2.73 mmol) were placed under 6.5 mL of 1,4-dioxane in a closed container, degassed, and the mixture was stirred at 120° C. for 2 hours. The mixture was cooled to room temperature, 50 mL water was added thereto, and the mixture was washed with a solution of chloroform/isopropanol (4:1). The mixture was dried over sodium sulfate and filtered and distilled under reduced pressure. The resulting oil was purified by column chromatography to obtain the title compound (78.5 mg, 20%).

Workup

customdegassed
temperatureThe mixture was cooled to room temperature
addition50 mL water was added
washthe mixture was washed with a solution of chloroform/isopropanol (4:1)
dry with materialThe mixture was dried over sodium sulfate
filtrationfiltered
distillationdistilled under reduced pressure
customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record: ord-71529af6c8114c10ada03efc0a5a7426
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835458B2

Reaction notes

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