Dichloromethane → methyl 2-bromo-6-chloro-1-isopropyl-3-methyl-1H-indole-4-carboxylate

HRID 516786Notes

Reaction equation

HRID 516786 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[C:5]2[C:6]([CH3:14])=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.C1C(=O)N([Br:26])C(=O)C1.CCOC(C)=O.C(Cl)Cl>CN(C=O)C>[Br:26][C:7]1[N:8]([CH:11]([CH3:12])[CH3:13])[C:9]2[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[C:5]=2[C:6]=1[CH3:14]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 67464586methyl 6-chloro-1-isopropyl-3-methyl-1H-indole-4-carboxylate

Product 1

HCID 67465593methyl 2-bromo-6-chloro-1-isopropyl-3-methyl-1H-indole-4-carboxylateYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 6-chloro-1-isopropyl-3-methyl-1H-indole-4-carboxylate (2.5 g, 9.41 mmol) in DMF (25 mL) was added NBS (1.7 g, 9.55 mmol). The reaction was stirred for 18 h then evaporated to dryness under vacuum. The reaction was purified by silica gel chromatography (Analogix, SF40-80 g, 0 to 5% EtOAc in hexanes) then (Analogix, SF25-60 g, 25% CH2Cl2 in hexanes) to give the product methyl 2-bromo-6-chloro-1-isopropyl-3-methyl-1H-indole-4-carboxylate (1.79 g, 5.19 mmol, 55.2% yield) as a clear oil. 1H NMR (400 MHz, DMSO-d6) 6=7.98 (d, J=1.8 Hz, 1H), 7.41 (d, J=1.8 Hz, 1H), 5.05 (dt, J=6.7, 13.4 Hz, 1H), 3.89 (s, 3H), 2.22 (s, 3H), 1.57 (d, J=7.1 Hz, 6H). MS(ES)+ m/e 344.0 [M+H]+.

Workup

  1. customthen evaporated to dryness under vacuum
  2. customThe reaction was purified by silica gel chromatography (Analogix

Sources & evidence

ORD record
ord-0e71a621cf194df5b27da53a5a5db8a5
Source dataset
uspto-grants-2015_08
Patent number
US09114141B2

Reaction notes

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