9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → HCID 67448518, compound

HRID 1853691Notes

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].[OH:18][CH2:19][CH:20]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH3:21]>>[OH:18][CH2:19][CH:20]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([C:2]2[C:3]3[C:4]4[CH:17]=[CH:16][S:15][C:5]=4[C:6](=[O:14])[NH:7][C:8]=3[CH:9]=[CH:10][C:11]=2[O:12][CH3:13])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH3:21]

Participants

Reactant 2

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

HCID 67452443HCID 67452443, compound

Product 1

HCID 67448518HCID 67448518, compoundYield 20%

Procedure

Following General Procedure B, 9-bromo-8-methoxy-thieno[2,3-c]quinolin-4(5H)-one) (530 mg, 1.8 mmol) was reacted with N-(1-hydroxypropan-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (750 mg, 2.02 mmol) to afford the desired product (150 mg, 20%) as a yellow solid: ESI MS m/z 445 [C21H20N2O5S2+H]+.

Sources & evidence

ORD record: ord-38de475ce8784b57875a8a35787126c9
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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