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

HRID 917780Notes

Reaction equation

HRID 917780 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[C:26]4[C:21](=[CH:22][C:23]([N+:27]([O-])=O)=[CH:24][CH:25]=4)[CH:20]=[CH:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>O1CCCC1.[Ni]>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[C:26]4[C:21](=[CH:22][C:23]([NH2:27])=[CH:24][CH:25]=4)[CH:20]=[CH:19]3)=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

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

Product 1

HCID 58962847(9H-Fluoren-9-yl)methyl 5-amino-1H-indole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-nitro-indole-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (4.16 g, 0.0108 mol) in 100 ml of tetrahydrofuran was treated with 1.0 g of sponge nickel catalyst (Activated Metals & Chemicals Co. A-7000, water wet) and hydrogenated in a Parr shaker hydrogenation apparatus (52 to 18 psig, room temperature). After 20 h, the resulting slurry was filtered and the filtrate was returned. Solvent was removed in vacuo to afford a brown oil (4.05 g, 106.6% y). NMR (CDCl3) δ 8.03 (br s, 1H), 7.78 (m, 3H), 7.63 (m,3H), 7.51 (d, J=3.2 Hz, 1H), 7.42 (m, 3H), 7.34 (m, 3H), 7.18 (d, J=8.3 Hz, 1H), 6.49 (d, J=2.3 Hz, 1H), 6.82 (d, J=2.0), 6.66 (dd, J=8.5, 2.2 Hz, 1H), 6.45 (d, J=3.7 Hz, 1H), 6.38 (m, 1H), 4.78 (br s, 2H), 4.43 (t, J=6.3 Hz, 1H), 4.12 (t, J=6.1 HZ, 1H), 4.03 (d, J=0.49 Hz, 2H), 3.76 (t, J=2.4 Hz, 1H), 1.85 (m, 1H). MS 355 [M+H].

Workup

  1. filtrationthe resulting slurry was filtered
  2. customSolvent was removed in vacuo
  3. customto afford a brown oil (4.05 g, 106.6% y)

Sources & evidence

ORD record
ord-f4fcc474a39f4b59b286a18d12dd2747
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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