Tetrahydrofuran → 6-chloro-5-nitro-1H-indole

HRID 1598004Notes

Reaction equation

C1COCC1.ClC1C=C2C(C=CN2)=CC=1F.[Cl:17][C:18]1[CH:26]=[C:25]2[C:21]([CH2:22][CH2:23][NH:24]2)=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28].B.N1C=CC=CC=1>>[Cl:17][C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[CH:23][NH:24]2)=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 2723995Borane;pyridine

HCID 27736486-Chloro-5-fluoro-1H-indole

HCID 189329026-chloro-5-nitro-2,3-dihydro-1H-indole

Product 1

HCID 189328576-chloro-5-nitro-1H-indole

Procedure

This material was produced from 6-chloro-5-nitro-oxindole (1 eq) and BH3 /THF (6 mol eq.) utilizing a method analogous to that described for 6-chloro-5-fluoro-indole (Preparation 29) in 99% yield (contaminated with some 6-chloro-5-nitro-indoline) and used directly in the subsequent borane/pyridine reduction.

Sources & evidence

ORD record: ord-b0500a985ce943bc94aa95966f762a00
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05736534

Reaction notes

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