Sodium Carbonate → HCID 57942668, compound

HRID 1438152Notes

Reaction equation

HRID 1438152 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:11]([CH2:14][CH3:15])(=[O:13])=[O:12].[C:16]([O:20][C:21]([N:23]1[CH:27]=[CH:26][CH:25]=[C:24]1B(O)O)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH2:14]([S:11]([C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[C:24]1[N:23]([C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[CH:27]=[CH:26][CH:25]=1)(=[O:13])=[O:12])[CH3:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 579428162-Bromo-1-(ethylsulfonyl)-4-nitrobenzene

Product 1

HCID 57942668HCID 57942668, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
97 °C

Procedure

To 100B (3.48 g, 11.8 mmol), 3A (3.0 g, 14.2 mmol) and sodium carbonate (23.7 mL, 2M, 47.4 mmol) in 1,2 dimethoxyethane (100 mL, flushed and degassed (3×) with nitrogen) was added Pd(PPh3)4 (2.74 g, 2.37 mmol). The reaction was heated to 97° C. for 3 h. The catalyst was filtered over celite and washed with ethyl acetate. The organic layer was washed with water, brine and then dried over sodium sulfate. The solvent was removed and the crude residue was purified by flash column chromatography to give 4.11 g of product 10° C. (91% yield). 1H NMR (400 MHz, Methanol-d4) δ ppm 1.09 (t, J=7.46 Hz, 3H) 1.25 (s, 9H) 2.87-3.04 (m, 2H) 6.24-6.44 (m, 2H) 7.46 (dd, J=3.30, 1.83 Hz, 1H) 8.24 (d, J=2.20 Hz, 1H) 8.31 (d, J=8.56 Hz, 1H) 8.45 (dd, J=8.80, 2.45 Hz, 1H).

Workup

  1. filtrationThe catalyst was filtered over celite
  2. washwashed with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. customthe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-87cea20bdadf402eb8b90d2229533630
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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