2-Nitrofluorene → 1-(4-Chloro-benzyl)-3-(2-nitro-fluoren-9-ylidenemethyl)-1H-indole

HRID 1476926Notes

Reaction equation

HRID 1476926 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)([O-:3])=[O:2].[Cl:17][C:18]1[CH:35]=[CH:34][C:21]([CH2:22][N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([CH:32]=O)=[CH:24]2)=[CH:20][CH:19]=1>CO>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][N:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([CH:32]=[C:7]3[C:6]4[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:16]=[CH:15][C:14]=4[C:13]4[C:8]3=[CH:9][CH:10]=[CH:11][CH:12]=4)=[CH:24]2)=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 118312-Nitrofluorene2×HCID 872445Oncrasin 1

Product 1

HCID 712720961-(4-Chloro-benzyl)-3-(2-nitro-fluoren-9-ylidenemethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
85 °C

Procedure

To a solution of 2-nitrofluorene (250 mg, 1.18 mmol) in 20 mL of methanol was added 1-(4-Chloro-benzyl)-1H-indole-3-carbaldehyde (382 mg, 1.42 mmol) and KF—Al2O3 (189 mg, 1.18 mmol). The resulting mixture was stirred at 85° C. for 18 hrs. After that, TLC showed that 2-nitrofluorene was gone, and many solids were suspended in MeOH. 260 mg of CYD-2-21 was obtained as a yellow solid after filtration and recrystallization from CH2Cl2. One isomer: 1H-NMR (600 MHz, d6-DMSO) δ 8.96 (s, 1H), 8.41 (s, 1H), 8.27 (m, 2H), 8.18 (m, 3H), 8.09 (d, 1H, J=7.2 Hz), 7.78 (d, 1H, J=7.8 Hz), 7.62 (d, 1H, J=7.8 Hz), 7.47 (m, 5H), 7.28 (t, 1H, J=7.2 Hz), 7.20 (t, 1H, J=7.2 Hz), 5.57 (s, 2H). Another isomer: 1H-NMR (600 MHz, d6-DMSO) δ 9.01 (s, 1H), 8.39 (s, 1H), 8.33 (s, 1H), 8.19 (m, 4H), 7.86 (d, 1H, J=8.4 Hz), 7.78 (d, 1H, J=7.8 Hz), 7.62 (d, 1H, J=7.8 Hz), 7.47 (m, 5H), 7.28 (t, 1H, J=7.2 Hz), 7.20 (t, 1H, J=7.2 Hz), 5.59 (s, 2H). 13C-NMR (150 MHz, d6-DMSO) δ 147.1, 146.6, 145.6, 142.9, 141.9, 141.0, 138.2, 138.0, 137.0, 136.8, 136.7, 136.4 (2C), 135.6, 132.7, 132.2, 132.1, 130.2, 129.9, 129.8, 129.7, 129.2, 129.1, 129.0 (2C), 128.4, 128.1 (2C), 127.9, 124.5, 124.1, 123.8, 123.2 (2C), 123.1, 122.4, 122.0, 121.7, 121.2, 121.0 (2C), 120.8, 120.6 (2C), 120.2, 118.8, 118.7, 116.2 (2C), 111.5, 111.4, 111.3 (2C), 49.4, 49.2.

Workup

  1. custom260 mg of CYD-2-21 was obtained as a yellow solid
  2. filtrationafter filtration and recrystallization from CH2Cl2

Sources & evidence

ORD record
ord-725b519bd6a9478d8cc6d057e0922e37
Source dataset
uspto-grants-2016_08
Patent number
US09402850B2

Reaction notes

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