3-Nitrophenylboronic Acid → 1-(6-Methoxy-3'-nitro-biphenyl-3-ylmethyl)-1H-indole

HRID 1632057Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.[N+:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21].C(OCC)(=O)C>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd+2]>[CH3:19][O:18][C:17]1[C:2]([C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:20]([O-:22])=[O:21])[CH:28]=2)=[CH:3][C:4]([CH2:5][N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A suspension of 1-(3-Bromo-4-methoxy-benzyl)-1H-indole (150 mg, 0.474 mmol), palladium bis(triphenylphosphine)dichloride (13.3 mg, 0.0190 mmol), and 3-nitrophenylboronic acid (94.9 mg, 0.569 mmol) in dioxane (10 mL) and 1 M aqueous sodium carbonate (1.1 mL) was stirred at 85° C. for 22 h. To the reaction was added ethyl acetate (30 mL). The organic suspension was washed with water (4×30 mL), brine (2×30 mL), dried over sodium sulfate, and the solvent removed under vacuum. The residue was purified by flash silica gel column chromatography (10% ethyl acetate in hexanes as the elutant) to yield 1-(6-Methoxy-3′-nitro-biphenyl-3-ylmethyl)-1H-indole P-010 (23.6 mg, 17% yield).

Workup

washThe organic suspension was washed with water (4×30 mL), brine (2×30 mL)
dry with materialdried over sodium sulfate
customthe solvent removed under vacuum
customThe residue was purified by flash silica gel column chromatography (10% ethyl acetate in hexanes as the elutant)

Sources & evidence

ORD record: ord-34387388fbb148b8842bc06f961d6909
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791267B2

Reaction notes

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