9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → HCID 68230117, compound

HRID 1853793Notes

Reaction equation

HRID 1853793 reaction equation
Br[C:2]1[C:3]2[C:4]3[CH:17]=[CH:16][S:15][C:5]=3[C:6](=[O:14])[NH:7][C:8]=2[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].CC1(C)C(C)(C)OB(/[CH:26]=[CH:27]/[CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:30]2)O1>>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:8]2[NH:7][C:6](=[O:14])[C:5]3[S:15][CH:16]=[CH:17][C:4]=3[C:3]=2[C:2]=1/[CH:26]=[CH:27]/[CH2:28][N:29]1[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:30]1

Participants

3

Reactant 2

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-oneHCID 86689495HCID 86689495, compound

Product 1

HCID 68230117HCID 68230117, compoundYield 47%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (530 mg, 1.7 mmol) was reacted with (E)-tert-Butyl 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]piperidin-3-ylcarbamate (320 mg, 0.88 mmol) to afford the desired product (190 mg, 47%) as a light brown solid: ESI MS m/z 456 [C24H29N3O4S+H]+.

Sources & evidence

ORD record
ord-fdea687dc4b5444299a4450eb387eade
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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