Sodium Bicarbonate → HCID 58893047, compound

HRID 1443082Notes

Reaction equation

HRID 1443082 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].Cl[C:18]1[CH:19]=[CH:20][N:21]2[C:26]([CH:27]=1)=[C:25]([CH2:28][CH3:29])[C:24]1[S:30][NH:31][C:32](=[O:33])[C:23]=1[C:22]2=[O:34]>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.CN(C)C=O>[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:18]2[CH:19]=[CH:20][N:21]3[C:26]([CH:27]=2)=[C:25]([CH2:28][CH3:29])[C:24]2[S:30][NH:31][C:32](=[O:33])[C:23]=2[C:22]3=[O:34])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734312(4-(Aminomethyl)phenyl)boronic acidHCID 11514675HCID 11514675, compound

Product 1

HCID 58893047HCID 58893047, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Under an atmosphere of argon, tetrakis(triphenylphosphine)palladium(0) (20.4 mg, 0.018 mmol), 4-aminomethylphenylboronic acid (110.0 mg, 0.587 mmol), and a 1 M aqueous solution of sodium bicarbonate (1.75 mL, 1.75 mmol) were added sequentially to a solution containing 7-chloro-9-ethyl-1-thia-2,4a-diazacyclopenta[b]naphthalene-3,4-dione (33.0 mg, 0.118 mmol) and dimethylformamide (3.0 mL). The resulting orange mixture was irradiated in a microwave for 15 min (110° C.; 300 W) to give a red mixture. The solvent is evaporated under reduced pressure (˜10 mm Hg, 50° C.), and the remaining orange solid is washed with diethyl ether (3×15 mL).

Workup

  1. customThe resulting orange mixture was irradiated in a microwave for 15 min (110° C.; 300 W)
  2. customto give a red mixture
  3. customThe solvent is evaporated under reduced pressure (˜10 mm Hg, 50° C.)
  4. washthe remaining orange solid is washed with diethyl ether (3×15 mL)

Sources & evidence

ORD record
ord-e455d0b2b2054ed99f8da0670ed40add
Source dataset
uspto-grants-2010_02
Patent number
US07659399B2

Reaction notes

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