Diisopropylethylamine → N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide

HRID 2056230Notes

Reaction equation

HRID 2056230 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11](Cl)=[O:12].[CH3:14][O:15][C:16]1[CH:22]=[C:21]([B:23]2[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]2)[CH:20]=[CH:19][C:17]=1[NH2:18].C(N(C(C)C)C(C)C)C>ClCCl>[CH3:14][O:15][C:16]1[CH:22]=[C:21]([B:23]2[O:24][C:25]([CH3:30])([CH3:31])[C:26]([CH3:29])([CH3:28])[O:27]2)[CH:20]=[CH:19][C:17]=1[NH:18][C:11]([C:3]1[N:2]([CH3:1])[C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 123033141-Methyl-1H-indole-2-carbonyl chlorideHCID 177502072-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 22347095N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamideYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 1-methyl-1H-2-indolecarbonyl chloride (5.44 g, 0.0281 mol) and 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (7.00 g, 0.0281 mol) in anhydrous dichloromethane (150 mL), N-ethyl-N,N-diisopropylamine (4.9 mL, 0.0309 mol) was added dropwise at 0° C. and the resulting solution was stirred at ambient temperature under an atmosphere of nitrogen for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between water (150 mL) and ethyl acetate (150 mL), The organic phase was washed with brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica using ethyl acetate/n-heptane (1:6)) as mobile phase to yield N2-[2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-methyl-1H-2-indolecarboxamide (8.0 g, 0.0197 mol) as a white solid.

Workup

  1. additionwas added dropwise at 0° C.
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between water (150 mL) and ethyl acetate (150 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-096c2185f9904b8ab9803c22f0985b1f
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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