Hydrochloric Acid → HCID 90720579, compound

HRID 11053Notes

Reaction equation

HRID 11053 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH:12]=[CH:13][C:14]1[CH:19]=[C:18]([N+]([O-])=O)[CH:17]=[C:16]([N+]([O-])=O)[CH:15]=1)=[CH:6]2.O1CCCCC1[O:32][CH2:33][CH2:34]Br.[ClH:36].[CH3:37][OH:38]>>[Cl:36][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([O:38][CH3:37])[C:14]=1[CH:13]=[CH:12][C:7]1[N:8]([CH2:34][CH2:33][OH:32])[C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 867601905-Methoxy-2-[2-(3,5-dinitrophenyl)ethenyl]-1H-indole

Product 1

HCID 90720579HCID 90720579, compoundYield 91%

Procedure

The reaction of 2-[2-(2-Chloro-6-methoxyphenyl)ethenyl]-5-methoxy-1H-indole (II; Ar=2-chloro-6-methoxyphenyl) (102) prepared as described in example 55 with 2-bromoethyl tetrahydro-2H-pyran-2-yl ether using the procedure described in example 38 followed by reaction of the crude product with 2N HCl in methanol gave 2-{2-[2-(2-Chloro-6-methoxyphenyl)ethenyl]-5-methoxy-1H-indol-1-yl}ethanol (III; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2OH) (109) in a 91% yield as a mixture of E/Z isomers, which was used without further purification.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-63c40e69daaa436491abcccf68ef7925
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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