Benzyl Bromide → ethyl 1-benzyl-5-nitro-3-phenyl-1H-indole-2-carboxylate

HRID 2118113Notes

Reaction equation

HRID 2118113 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-:3])=[O:2].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[CH2:24]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 741309ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 69231884ethyl 1-benzyl-5-nitro-3-phenyl-1H-indole-2-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate (1.0 g, 3.23 mmol) and benzyl bromide (0.60 g, 3.5 mmol) in THF (50 mL) was treated with Cs2CO3 (3.26 g, 10 mmol) and heated to a gentle reflux for 16 h. After cooling to room temperature the reaction was quenched by addition of water and then partitioned between water and EtOAc. The organic phase was dried over MgSO4, and concentrated to yield ethyl 1-benzyl-5-nitro-3-phenyl-1H-indole-2-carboxylate as a yellowish solid (1.20 g, 93%): 1H NMR (DMSO-d6) δ 0.93 (t, J=7.0 Hz, 3H), 4.11 (q, J=7.0 Hz, 2H), 5.91 (s, 2H), 7.12 (d, J=8.3 Hz, 2H), 7.30-7.32 (m, 3H), 7.50-7.55 (m, 5H), 7.92 (d, J=9.2 Hz, 1H), 8.22 (dd, J=9.2, 2.0 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H); MS (EI) m/z 400.1 (MH+); Anal. calcd for C24H20N2O4: C, 71.99; H, 5.03; N, 7.00. Found: C, 71.77; H, 5.14; N, 6.71.

Workup

  1. temperatureheated to
  2. temperaturea gentle reflux for 16 h
  3. customwas quenched by addition of water
  4. custompartitioned between water and EtOAc
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c9db3c09429a432c8e9fe7057e950da0
Source dataset
uspto-grants-2008_10
Patent number
US07442805B2

Reaction notes

Loading…