Morpholine → HCID 11106869, compound

HRID 2180362Notes

Reaction equation

CC([O-])(C)C.[Na+].[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>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]>[C:22]([C:19]1[CH:20]=[CH:21][C:16]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[CH:17][CH:18]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of Pd2(dba)3 [92 mg, 0.1 mmol (4.6 mg, 0.005 mmol, 2 mol % Pd per reaction)], ligand 1 (see FIG. 1) [168 mg, 0.4 mmol (8.4 mg, 0.02 mmol, 4 mol % per reaction)] and NaOt-Bu [40 mg, 0.4 mmol (2 mg, 0.02 mmol, 4 mol % per reaction)] were stirred in 10 mL DME (anhy). After 10 minutes, 0.5 mL of the solution was added via syringe to a test tube containing (under an Argon atmosphere) K3PO4 (148 mg, 0.7 mmol), 1-bromo-4-tert-butylbenzene (86 μL, 0.5 mmol), and morpholine (52 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 GC yield was calculated to be 12%.

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 GC yield

Sources & evidence

ORD record: ord-1e8e9c8a2c394beeb103fcf0963e9612
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06888029B2

Reaction notes

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