7-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one → HCID 66835214, compound

HRID 61927Notes

Reaction equation

HRID 61927 reaction equation
COC1C=C2C(CCC(=O)C2(C)C)=CC=1.Br[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[OH:24].[OH:25][C:26]1[CH:27]=[CH:28][C:29]2[C:41](=[O:42])[C:40]3C4C(=CC(C#N)=CC=4)N[C:32]=3[C:31](C)(C)[C:30]=2[CH:47]=1>>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]2[C:40]3[C:41](=[O:42])[C:29]4[C:30]([CH2:31][C:32]=3[O:24][C:18]=2[CH:19]=1)=[CH:47][C:26]([OH:25])=[CH:27][CH:28]=4

Participants

4

Reactant 3

HCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-oneHCID 132842722-Bromo-5-chlorophenolHCID 668338618-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Product 1

HCID 66835214HCID 66835214, compound

Procedure

The compounds described in the following Table 43 were synthesized according to the method shown below. According to the method used for the preparation of Compound Z10, Z11 and Z12, 3-chloro-8-methoxy-6H-benzo[b]naphtho[2,3-d]furan-11-one was prepared from Compound A2 and 2-bromo-5-chlorophenol. Subsequently, demethylation was carried out according to the method that is used for the preparation of Compound A6, and thus 3-chloro-8-hydroxy-6H-benzo[b]naphtho[2,3-d]furan-11-one was obtained. Thereafter, according to Mitsunobu reaction that is used for the preparation of Compound A7-1 or the alkylation method that is used for the preparation of A7-17, a corresponding side chain was introduced and, if necessary, functional group modification such as deprotection, etc. was carried out to prepare the compounds listed below.

Workup

  1. customwere synthesized

Sources & evidence

ORD record
ord-fd910d352207495fbb5a80f9743cddc1
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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