Methyl iodide → Benzyl 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

HRID 2090399Notes

Reaction equation

HRID 2090399 reaction equation
CI.[CH3:3][C:4]1([CH3:26])[C:8]([CH3:10])([CH3:9])[O:7][B:6]([C:11]2[CH:12]=[C:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[NH:14][CH:15]=2)[O:5]1.[C:27](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH3:27][N:14]1[CH:15]=[C:11]([B:6]2[O:5][C:4]([CH3:26])([CH3:3])[C:8]([CH3:9])([CH3:10])[O:7]2)[CH:12]=[C:13]1[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 59402337HCID 59402337, compound

Product 1

HCID 59402364Benzyl 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl iodide (0.27 mL, 4.3 mmol) was added to a mixture of benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate (0.7 g, 2 mmol) and cesium carbonate (1.4 g, 4.3 mmol) in DMF (5.0 mL) and then the reaction was stirred at r.t. for 1 h. LCMS showed the reaction was complete. The mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (0-10%) to afford the desired product. LCMS (M+H)+: m/z=342.2.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (0-10%)

Sources & evidence

ORD record
ord-c94fb17e71e149e3b2973035b0e5f699
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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