Sodium Carbonate → HCID 178433248, compound

HRID 382070Notes

Reaction equation

HRID 382070 reaction equation
Br[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH3:21])/[C:5](=[O:14])[NH:6]2.C[Si](C)(C)N[Si](C)(C)C.[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CN(C=O)C>[CH3:21][C:17]1[N:18]=[CH:19][NH:20][C:16]=1/[CH:15]=[C:4]1\[C:5](=[O:14])[NH:6][C:7]2[C:3]\1=[C:2]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=2

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 13838HexamethyldisilazaneHCID 66827Phenylboronic AcidHCID 178433246HCID 178433246, compound2×

Product 1

HCID 178433248HCID 178433248, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Using Method S above, (Z)-4-bromo-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-2H-indol-2-one (100 mg, 0.29 mmol) (Starting Material 9 above) was first treated with 1,1,1,3,3,3-hexamethyidisilazane (1.53 g, 9.5 mmol) (Aldrich) then coupled with phenyl boronic acid (52.4 mg, 0.43 mmol) (Aldrich) using DPPFPdCl2 (11.7 mg) (Aldrich) as catalyst in aqueous 2M Na2CO3 (0.29 mL, 0.58 mmol), DMF (3 mL) and DME (3 mL) at reflux for 1 day to yield (Z)-1,3-dihydro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-4-phenyl-2H-indol-2-one (yield 9 mg, 9%).

Workup

  1. temperatureat reflux for 1 day

Sources & evidence

ORD record
ord-256ba74d7edd4dc4a250b58e05aab522
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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