5-Benzyloxyindole → 5-Phenylmethoxy-1-(4-pyridinylamino)-1H-indole

HRID 2248485Notes

Reaction equation

HRID 2248485 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([NH2:18])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1C=C2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[CH:30]2)C1C=CC=CC=1.NOS(O)(=O)=O.Cl.ClC1C=CN=CC=1>CN1CCCC1=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([NH:18][C:35]1[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=1)[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 146245-BenzyloxyindoleHCID 76284hydroxylamine-O-sulfonic acidHCID 818524-Chloropyridine hydrochlorideHCID 149882975-(Benzyloxy)-1H-indol-1-amine

Product 1

HCID 149882825-Phenylmethoxy-1-(4-pyridinylamino)-1H-indole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The title compound was prepared from 5-benzyloxy-1H-indol-1-amine (which had been prepared from 5-benzyloxy-1H-indole and hydroxylamine-O-sulfonic acid in substantially the same manner as in Example 25) and 4-chloropyridine hydrochloride in N-methyl-2-pyrrolidinone at 70° C. for 1.5 hours in substantially the same manner as in Example 1, m.p. 143°-145° C.

Sources & evidence

ORD record
ord-3510be0915fb41b5bdc255a698a33eb1
Source dataset
uspto-grants-1991_08
Patent number
US05039811

Reaction notes

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