Potassium Phosphate, Tribasic → methyl 1-(4-pyridin-2-yl benzyl)-1H-indole-7-carboxylate

HRID 1909879Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:28]=[CH:27][C:12]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][C:21]=4[C:23]([O:25][CH3:26])=[O:24])[CH:16]=[CH:15]3)=[CH:11][CH:10]=2)O1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1OS(C(F)(F)F)(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[Pd](Cl)Cl.O.O1CCOCC1>[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][C:21]=3[C:23]([O:25][CH3:26])=[O:24])[CH:16]=[CH:15]2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To methyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]-1H-indole-7-carboxylate (0.30 g), pyridin-2-yltrifluoromethanesulfonate (0.35 g), tripotassium phosphate (0.49 g), palladium(II) chloride (27 mg), and biphenyl-2-yl(dicyclohexyl)phosphine (0.11 g) were added dioxane (12 mL) and water (3.0 mL), followed by stirring at 100° C. for 4 hours. The reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate=5/1-4/1) to obtain methyl 1-(4-pyridin-2-yl benzyl)-1H-indole-7-carboxylate (0.15 g).

Workup

customThe reaction mixture was purified by silica gel column chromatography (hexane/ethyl acetate=5/1-4/1)

Sources & evidence

ORD record: ord-cf64c48e514e45cea79144abe207e379
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598355B2

Reaction notes

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