Triethylamine → HCID 10360831, compound

HRID 2100300Notes

Reaction equation

HRID 2100300 reaction equation
[N:1]1([C:7]2[O:8][C:9]3[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[C:22]([CH3:29])[CH:21]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N:1]1([C:7]2[O:8][C:9]3[C:17]([O:18][C:23]4[CH:24]=[CH:25][C:20]([F:19])=[CH:21][C:22]=4[CH3:29])=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 15953444HCID 15953444, compound

Product 1

HCID 10360831HCID 10360831, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(4-morpholinyl)-8-hydroxy-4H-1-benzopyran-4-one (77 mg, 0.31 mmol), 4-fluoro-2-methylphenylboronic acid (48 mg, 0.31 mmol) and copper acetate (57 mg, 0.31 mmol) suspended in dichloromethane (3.1 ml) was added triethylamine (216 uL, 1.56 mmol) and the mixture was stirred at room temperature for 24 h. The solvent was removed and the product chromatographed through a silica column with 0-10% methanol in dichloromethane to yield an off white solid (37 mg).

Workup

  1. customThe solvent was removed
  2. customthe product chromatographed through a silica column with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-e2df8f0922bf43e498bb478fad1624ab
Source dataset
uspto-grants-2009_08
Patent number
US07572791B2

Reaction notes

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