Sodium Carbonate → HCID 59852603, compound

HRID 2373828Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH:12][C:13]([C:15]2[C:24]([OH:25])=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[O:14])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[N+:26]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)([O-:28])=[O:27].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:32]2[CH:33]=[CH:34][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][CH:31]=2)=[CH:3][C:4]=1[CH2:10][CH2:11][NH:12][C:13]([C:15]1[C:24]([OH:25])=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)=[O:14]

Participants

Conditions

Temperature: 80 °C

Procedure

To 0.05 g (0.1 mmol) of above resin-bound N-2-(3-bromo-6-methoxyphenyl)ethyl-3-hydroxyl-2-naphthamide in 2.0 mL of DME were added 36.6 mg (0.3 mmol) of 4-nitrophenylboronic acid, 30 mg (0.03 mmol) of Pd(PPh3)4, and 0.3 mL (0.6 mmol) of 2N Na2CO3 solution. The mixture was heated to 80° C. for 12 h. The resin was washed with H2O, DMF, MeOH, DCM three times of each and cleaved with TMSBr/TFA/DCM (1:1:5) at rt for 4 h. The residue obtained after removing the solvent was purified by chromatography (100% methylene chloride) to give 22 mg of the title compound.

Workup

washThe resin was washed with H2O, DMF, MeOH, DCM three times of each and
customThe residue obtained
customafter removing the solvent
customwas purified by chromatography (100% methylene chloride)

Sources & evidence

ORD record: ord-5157bd70858c406991c9f1be39c46547
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459472B2

Reaction notes

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