1,1'-Biphenyl, 4-(bromomethyl)- → Ethyl 1-(1,1'-biphenyl-4-ylmethyl)-5-nitro-3-phenyl-1H-indole-2-carboxylate

HRID 915347Notes

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[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][CH:27]=1>>[C:29]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:28]=[CH:27][C:26]([CH2:25][N:9]2[C:10]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:8]2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:31][CH:30]=1

Participants

Reactant 2

HCID 2577161,1'-Biphenyl, 4-(bromomethyl)-

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

Product 1

HCID 69228457Ethyl 1-(1,1'-biphenyl-4-ylmethyl)-5-nitro-3-phenyl-1H-indole-2-carboxylate

Procedure

Ethyl 1-(1,1′-biphenyl-4-ylmethyl)-5-nitro-3-phenyl-1H-indole-2-carboxylate was prepared from ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate and 4-bromomethylbiphenyl according to the procedure of Example 1 Step 1 as a yellowish solid: 1H NMR (DMSO-d6) δ 0.95 (t, J=7.0 Hz, 3 H), 4.13 (q, J=7.0 Hz, 2 H), 5.96 (s, 2 H), 7.30-7.32 (m, 14 H), 7.62 (d, J=2.3 Hz, 1 H), 8.25 (d, J=2.8 Hz, 1 H), 8.36 (s, 1 H); MS (ESI) m.z 477 (MH+); HRMS calcd for C30H25N2O4: 477.1815; found (ESI+): 477.1806; Anal. calcd for C30H24N2O4: C, 75.62; H, 5.08; N, 5.88. Found: C, 75.25; H, 5.18; N, 5.47.

Sources & evidence

ORD record: ord-c1f049a441f34e338ed0076137800fc6
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265148B2

Reaction notes

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