2,6-Dimethylaniline → HCID 12545262, compound

HRID 2180356Notes

Reaction equation

CC([O-])(C)C.[Na+].[O-]P([O-])([O-])=O.[K+].[K+].[K+].Cl[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23].[CH3:25][C:26]1[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:27]=1[NH2:28]>COCCOC.CCOCC.CCCCCCCCCCCC.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]>[CH3:25][C:26]1[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:27]=1[NH:28][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of ligand 1 (see FIG. 1) [42 mg, 0.1 mmol (8.4 mg, 0.02 mmol, 4 mol % per reaction)] and NaOt-Bu [10 mg, 0.1 mmol (2 mg, 0.02 mmol, 4 mol % per reaction)] were stirred in 5 mL DME (anhy). After 10 minutes, 1 mL of the solution was added via syringe to a test tube containing (under an Argon atmosphere) Pd2(dba)3 (4.6 mg, 0.005 mmol, 2 mol % Pd), K3PO4 (148 mg, 0.7 mmol), 2-chloronitrobenzene (79 mg, 0.5 mmol), and 2,6-dimethylaniline (74 μL, 0.6 mmol). The test tube was capped (with a proper cap-no rubber septa) and heated at 100° C. for 18 hours. The reaction mixture was allowed to cool to r.t., diluted with ether and dodecane was added as an internal standard. The reaction mixture was purified by column chromatography (5% EtOAc/hexanes) to yield 110 mg (91% yield) of the product.

Workup

customThe test tube was capped (with a proper cap-no rubber septa) and
temperatureto cool to r.t.
additionwas added as an internal standard
customThe reaction mixture was purified by column chromatography (5% EtOAc/hexanes)

Sources & evidence

ORD record: ord-8c3e2445f0eb400aafc422a8d78ccd85
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06888029B2

Reaction notes

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