Sodium Carbonate → HCID 22271979, compound

HRID 488665Notes

Reaction equation

Br[C:2]1[C:3]([OH:25])=[C:4]([C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[Na+].[Na+].[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.[Pd].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.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>[C:21]([O:20][C:18]([NH:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:2]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:3]([OH:25])[C:4]=1[C:5]([O:7][CH3:8])=[O:6])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of methyl 3-bromo-6-{4-[(tert-butoxycarbonyl)amino]butoxy}-2-hydroxybenzoate (56 mg, 0.134 mmol), tetrakis(triphenylphosphine) palladium (7 mg), 2M Na2CO3 (134 μL, 0.268 mmol) in toluene (1 mL) and ethanol (0.5 mL) was added phenylboronic acid (18 mg, 0.147 mmol). The reaction mixture was heated to 80° C. in a sealed tube overnight, taken up in ethyl acetate, washed with aqueous NaHCO3, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified on silica gel with hexane/ethyl acetate to provide the titled compound (23 mg). MS (ESI(+)) m/e 416 (M+H)+.

Workup

washwashed with aqueous NaHCO3
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record: ord-85c85e9b432b4c359e93f4ba523f40b7
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972340B2

Reaction notes

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