Sodium Carbonate → 5-(3-Benzyloxy-7-vinylnaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 643874Notes

Reaction equation

HRID 643874 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N:20]2[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]2)=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14](Br)[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28](OB(C=C)OCCCC)[CH2:29]CC.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH2:1]([O:8][C:9]1[C:10]([N:20]2[S:24](=[O:26])(=[O:25])[NH:23][C:22](=[O:27])[CH2:21]2)=[CH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([CH:28]=[CH2:29])[CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 236543Dibutyl Vinylboronate (stabilized with Phenothiazine)HCID 667506335-(3-(Benzyloxy)-7-bromonaphthalen-2-yl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 667506375-(3-Benzyloxy-7-vinylnaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

To a microwave vial containing 5-(3-benzyloxy-7-bromonaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (Example 3, step D) (0.21 g, 0.46 mmol), vinylboronic acid dibutyl ester (0.20 mL, 0.92 mmol), and PS-tetrakistriphenylphosphine palladium (0.36 mg, 0.046 mmol) in DME (4 mL) is added Na2CO3 (2.0M, 0.92 mL, 1.83 mmol). This is stirred in the microwave at 110° C. for 10 min, at which time LC/MS reveals complete conversion to the desired product. The resin-bound palladium is removed by filtration and the filtrate is concentrated in vacuo, and purified by reverse-phase Biotage MPLC to afford 5-(3-benzyloxy-7-vinylnaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a light brown oil.

Sources & evidence

ORD record
ord-7f6b9c684e8b463f941fa3921bd17bb1
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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