Water → (9H-Fluoren-9-yl)methyl 5-nitro-1H-indole-1-carboxylate

HRID 917779Notes

Reaction equation

HRID 917779 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].C([O-])([O-])=O.[Na+].[Na+].[C:19](OC(Cl)=O)([O:21][CH2:22][CH:23]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20].O>O1CCOCC1>[CH:34]1[C:35]2[CH:23]([CH2:22][O:21][C:19]([N:9]3[C:10]4[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=4)[CH:7]=[CH:8]3)=[O:20])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]=2[CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 225235-NitroindoleHCID 11012114HCID 11012114, compound

Product 1

HCID 58962846(9H-Fluoren-9-yl)methyl 5-nitro-1H-indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Nitroindole (2.0 g, 12.3 mmol) was dissolved in dioxane (25 mL) and 10% wt./vol Na2CO3 solution (2.5 g, water 25 mL) was added. FMOC-chloroformate (3.19 g, 12.3 mmol) was added to the mixture and the reaction was stirred overnight. The reaction mixture was transferred into water, filtered as a yellow solid and dried in vacuum oven at 50° C. for 2 hours. Obtained (4.07 g, 86% y). NMR (400 MHz, CDCl3), δ 8.61 (d, J=2.2 Hz, 1H), 8.43 (d, J=2.2 Hz, 1H), 8.12 (dd, J=7.3, 5.1 Hz, 1H), 8.02 (d, J=8.3 Hz, 1H), 7.82 (d, J=7.6 Hz, 2H), 7.76 (d, J=7.6 Hz, 2H), 7.62 (m, 4H), 7.60-7.30 (m, 8H), 6.74-6.69 (m, 2H), 4.94 (d, J=5.4 Hz, 2H), 4.41 (t, J=5.1 Hz, 1H), 4.05 (d, J=5.6 Hz, 2H). MS 384 [M−H] APCI.

Workup

  1. filtrationfiltered as a yellow solid
  2. customdried in vacuum oven at 50° C. for 2 hours
  3. customObtained (4.07 g, 86% y)

Sources & evidence

ORD record
ord-92b44a9e7f6b436a8d4b4743a44b0eb1
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

Loading…