N-bromobutanimide → Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1713922Notes

Reaction equation

HRID 1713922 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:27][C:8]1[NH:9][C:10]2[C:15]([C:7]=1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11230631Methyl 3-cyclohexyl-1H-indole-6-carboxylate

Product 1

HCID 11175076Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylateYield 49.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution (0.14 M) of methyl 3-cyclohexyl-1H-indole-6-carboxylate (from Step 2) in CCl4 was added freshly crystallized NBS (1.1 eq.) portionwise over a period of 1 h at RT. The resulting mixture was stirred for 2 h at RT, then washed with water (3×) and a saturated aqueous solution of sodium thiosulfate (2×). After phase cut, the aqueous phases were back-washed with EtOAc and die combined organic phases dried over Na2SO4 and evaporated. The resulting brown solid was dissolved in hot DCM and filtered rapidly over a pad of silica-gel using DCM as the eluant to give the title compound (49.6%) as a solid, 1H NMR (300 MHz, DMSO-d6, 300 K) δ 1.32-1.48 (m, 3H), 1.65-1.99 (m, 7H), 2.69-2.89 (m, 1H), 3.89 (s, 3H), 7.59 (d, J 7.6, 1H), 7.75 (d, J 7.6, 1H), 7.92 (s, 1H), 12.02 (br s, 1H); MS (ES+) m/z 337 (M+H)+.

Workup

  1. washwashed with water (3×)
  2. washAfter phase cut, the aqueous phases were back-washed with EtOAc
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. dissolutionThe resulting brown solid was dissolved in hot DCM
  6. filtrationfiltered rapidly over a pad of silica-gel

Sources & evidence

ORD record
ord-a55f592f4d554e85a483f0337e90fc66
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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