p-Fluoronitrobenzene → HCID 59422544, compound

HRID 500019Notes

Reaction equation

HRID 500019 reaction equation
IC1C=CC(N2C3C=CC=C(O)C=3CC2)=CC=1.F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.[CH3:28][O:29][C:30]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:31]=1[CH:32]=[CH:33][NH:34]2.C([O-])([O-])=O.[Cs+].[Cs+]>>[CH3:28][O:29][C:30]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:31]=1[CH:32]=[CH:33][N:34]2[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 1383634-Methoxy-1H-indoleHCID 59422571HCID 59422571, compound

Product 1

HCID 59422544HCID 59422544, compound

Procedure

The synthesis of 1-(4-iodophenyl)indolin-4-ol (92) is provided in Reaction Scheme 4b. The reaction of 1-fluoro-4-nitrobenzene and 4-methoxy-1H-indole in the presence of Cs2CO3 gave 4-methoxy-1-(4-nitrophenyl)-1H-indole (88), which was reduced with H2/Pd to yield 4-(4-methoxy-1H-indol-1-yl)benzenamine (89). The amino group of 89 was converted via the Sandmeyer reaction to 1-(4-iodophenyl)-4-methoxy-1H-indole (90) which on reduction with sodium borocyanohyride gave 1-(4-iodophenyl)-4-methoxyindoline (91). The indoline 91 was demethylated with BBr3 to provide the desired 92.

Workup

  1. customis provided in Reaction Scheme 4b

Sources & evidence

ORD record
ord-e8e694d3ff8b4fc4a4890bf8c1a21a9d
Source dataset
uspto-grants-2010_08
Patent number
US07767834B2

Reaction notes

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