Bromodiphenylmethane → Ethyl 1-benzhydryl-5-nitro-3-phenyl-1H-indole-2-carboxylate

HRID 2118130Notes

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].Br[CH:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH:25]([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:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Reactant 2

HCID 236603Bromodiphenylmethane

HCID 741309ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 69228492Ethyl 1-benzhydryl-5-nitro-3-phenyl-1H-indole-2-carboxylate

Procedure

Ethyl 1-benzhydryl-5-nitro-3-phenyl-1H-indole-2-carboxylate was prepared from ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate and bromodiphenylmethane according to the procedure of Example 1 Step 1 as a yellowish solid: 1H NMR (CDCl3) δ 0.92 (t, J=7.1 Hz, 3H, 4.08 (q, J=7.1 Hz, 2H, 6.86 (d, J=9.4 Hz, 1H, 7.20-7.50 (m, 15H, 7.89 (dd, J=9.3, 2.3 Hz, 1H, 7.97 (s, 1H, 8.47 (d, J=2.3 Hz, 1H, MS (ESI) m/z 477 (MH+); HRMS calcd for C30H25N2O4: 477.1812; found (ESI+): 477.1808.

Sources & evidence

ORD record: ord-6c54e36043804bad82616a8f022e4285
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442805B2

Reaction notes

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