Potassium Carbonate → Methyl 4,6-dichloro-8-methylthieno[2,3-b]indole-2-carboxylate

HRID 1957206Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([Cl:12])[CH:7]=[C:8]([Cl:11])[CH:9]=2)[C:4]([CH:13]=O)=[C:3]1Cl.C([O-])([O-])=O.[K+].[K+].[SH:22][CH2:23][C:24]([O:26][CH3:27])=[O:25]>>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[C:10]2[C:5]=1[C:4]1[CH:13]=[C:23]([C:24]([O:26][CH3:27])=[O:25])[S:22][C:3]=1[N:2]2[CH3:1]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 16907Methyl Thioglycolate

HCID 190689781-Methyl-2,4,6-trichloroindole-3-carbaldehyde

Product 1

HCID 19068958Methyl 4,6-dichloro-8-methylthieno[2,3-b]indole-2-carboxylateYield 32.5%

Procedure

Prepared from (48) (6.5 g), K2CO3 (9.59 g) and methyl 2-mercaptoacetate (3.82 ml) yielding (53) 2.5 g (32.5%). M.p. 231°-232° C. The product was purified by cromatography on silicagel using toluene as eluent. The compound was crystallized by trituration with methanol.

Sources & evidence

ORD record: ord-843bd6fa4dcf47ba8413109ae8f4241f
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783575

Reaction notes

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