Sodium Carbonate → HCID 131735834, compound

HRID 2206109Notes

Reaction equation

Br[C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][N:7]=[C:6]([O:13][CH3:14])[C:5]=2[N:4]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:3]=1.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:14][O:13][C:6]1[C:5]2[N:4]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:3]=[C:2]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH3:23])[C:10]=2[C:9]([C:11]#[N:12])=[CH:8][N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-bromo-7-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine-4-carbonitrile (1.30 g) in toluene (17 mL) were added 2-dicyclohexyl phosphino-2′,4′,6′-triisopropylbiphenyl (0.486 g), tris(dibenzylideneacetone)dipalladium(0) (0.311 g), (2-methylphenyl)boronic acid (0.693 g) and 2M aqueous sodium carbonate solution (5.10 mL) at room temperature, and the mixture was stirred at 90° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane). The obtained fraction was treated with activated carbon, and concentrated under reduced pressure to give the title compound (1.20 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)
additionThe obtained fraction was treated with activated carbon
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e0eac781cc234aadba06799c601ca994
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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