Ethyl bromoacetate → Ethyl 4,5-dihydro-4-oxothiopyrano[3,2-b]indole-5-acetate

HRID 437786Notes

Reaction equation

[S:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[C:4](=[O:14])[CH:3]=[CH:2]1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[O:14]=[C:4]1[C:5]2[N:6]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[S:1][CH:2]=[CH:3]1

Participants

Reactant 2

HCID 7748Ethyl bromoacetate

HCID 20326608Thiopyrano[3,2-b]indol-4(5H)-one

Product 1

HCID 20326604Ethyl 4,5-dihydro-4-oxothiopyrano[3,2-b]indole-5-acetate

Procedure

By the same method as described in Example 7, 4.8 g of thiopyrano-[3,2-b]indol-4(5H)-one is alkylated with ethyl bromoacetate to give 6.0 g of product, mp 163°-165° C., after recrystallization from ethyl acetate.

Sources & evidence

ORD record: ord-3114975ca12d450eb907b8bc2f983797
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04032537

Reaction notes

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