Sodium Carbonate → HCID 22147962, compound

HRID 1823920Notes

Reaction equation

HRID 1823920 reaction equation
Br[C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([CH3:12])[C:3]=1[NH2:4].[C:13]1(B(O)O)[CH:18]=[CH:17]C=[CH:15][CH:14]=1.[C:22]([O-])([O-])=O.[Na+].[Na+].CCO.O>COCCOC.ClCCl.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>[CH3:22][C:2]1[C:3]([NH2:4])=[C:5]([C:12]2[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=2)[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 2930732-bromo-6-methyl-4-nitroanilineHCID 19096565Water ethanol

Product 1

HCID 22147962HCID 22147962, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-bromo-6-methyl-4-nitroaniline (100 mg, 0.43 mmole), phenyl boronic acid (81 mg, 0.66 mmole), 2M Na2CO3(aq) (660 μL), Pd(PPh3)4 (4 mg, 0.0033 mmole) in DME(2.4 mL) containing 1.0:1.3 EtOH/H2O (1.4 mL) was placed in a microwave tube and degassed for 5 minutes. The tube was then capped and irradiated with microwaves (CEM Discover) for 20 minutes at 110° C. The crude reaction mixture was diluted with dichloromethane (10 mL) and washed with saturated NaHCO3 solution (3×20 mL). The organic layer was dried (MgSO4), filtered and concentrated in-vacuo to afford a crude solid, this was then purified further by flash chromatography (100% dichloromethane) to yield the desired pure (91 mg) as a bright yellow solid. 1H NMR (400 MHz, CDCl3) δ 2.25(3H, s), 4.42(2H, br s), 7.39(3H, m), 7.50(2H, m), 7.97(1H, s), 8.12(1H, s). MS (ES+): m/e=229, (ES−): m/e=227.

Workup

  1. customwas placed in a microwave tube
  2. customdegassed for 5 minutes
  3. customThe tube was then capped
  4. customirradiated with microwaves (CEM Discover) for 20 minutes at 110° C
  5. customThe crude reaction mixture
  6. washwashed with saturated NaHCO3 solution (3×20 mL)
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in-vacuo
  10. customto afford a crude solid
  11. customthis was then purified further by flash chromatography (100% dichloromethane)
  12. customto yield the desired pure (91 mg) as a bright yellow solid

Sources & evidence

ORD record
ord-ff81370191ed416fa02f0420ed5a76a6
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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