Sodium Carbonate → HCID 57942715, compound

HRID 1515497Notes

Reaction equation

HRID 1515497 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]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12].[C:17]([O:21][C:22]([N:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O)=[O:23])([CH3:20])([CH3:19])[CH3:18].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>[CH:14]([S:11]([C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[C:25]1[N:24]([C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[CH:28]=[CH:27][CH:26]=1)(=[O:13])=[O:12])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 57942709HCID 57942709, compound

Product 1

HCID 57942715HCID 57942715, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 1C (3.0 g, 9.7 mmol), 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid (2.5 g, 11.7 mmol, prepared according to the procedure in Synthesis, 1991, 613-615.) and sodium carbonate (19.5 mL, 2M, 38.9 mmol) in 1,2-dimethoxyethane (100 mL, flushed and degassed (3×) with nitrogen) was added Pd(PPh3)4 (2.2 g, 1.9 mmol) under nitrogen. The reaction was heated to 95° 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 3.68 g of 1D (96% yield). 1H NMR (400 MHz, Methanol-d4) δ ppm 1.01 (d, J=6.85 Hz, 3H) 1.15 (d, J=6.85 Hz, 3H) 1.20 (d, J=7.83 Hz, 9H) 3.00 (m, 1H) 6.29 (m, 2H) 7.41 (dd, J=3.18, 1.71 Hz, 1H) 8.20 (d, J=2.20 Hz, 1H) 8.25 (d, J=8.56 Hz, 1H), 8.41 (dd, J=8.68 Hz, 2.32 Hz, 1H).

Workup

  1. customprepared
  2. customaccording to the procedure in Synthesis, 1991, 613-615
  3. filtrationThe catalyst was filtered over Celite®
  4. washwashed with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed
  8. customthe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-37ce3161f869487e96e1ac0ffa777bb5
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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