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

HRID 245656Notes

Reaction equation

HRID 245656 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)[CH:7]=[CH:6][C:4]=1[NH2:5].[CH3:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[C:29](Cl)=[O:30]>CN(C)C1C=CN=CC=1.ClCCl.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)[CH:7]=[CH:6][C:4]=1[NH:5][C:29]([C:21]1[N:20]([CH3:19])[C:28]2[C:23]([CH:22]=1)=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:30]

Participants

6

Reactant 2

HCID 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 92.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (4.01 mmol, 1 g) and 4-dimethylaminopyridine (0.401 mmol, 0.049 g) in dichloromethane (5 ml) and pyridine (5 ml) was added 1-methyl-1H-indole-2-carbonyl chloride (5.22 mmol, 1.010 g) and this solution was stirred at room temperature for four days. The reaction mixture was concentrated and coevaporated with toluene. To the residue dichloromethane and water were added. The organic layer was separated, dried (sodium sulfate) and concentrated in vacuo. Purification using flash chromatography (silica gel, dichloromethane) yielded N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide (1.5 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionTo the residue dichloromethane and water were added
  3. customThe organic layer was separated
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-f87d8cdcc57c41dd9651660f3ea1337d
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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