9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one → tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutyl(methyl)carbamate

HRID 1853689Notes

Reaction equation

HRID 1853689 reaction equation
Br[C:2]1[C:3]2[C:4]3[CH:18]=[CH:17][S:16][C:5]=3[C:6](=[O:15])[NH:7][C:8]=2[C:9]([CH3:14])=[CH:10][C:11]=1[O:12][CH3:13].[CH3:19][N:20]([CH2:28][CH:29]([C:33]1[CH:38]=[CH:37][C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][CH:34]=1)[CH:30]([CH3:32])[CH3:31])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>>[CH3:13][O:12][C:11]1[CH:10]=[C:9]([CH3:14])[C:8]2[NH:7][C:6](=[O:15])[C:5]3[S:16][CH:17]=[CH:18][C:4]=3[C:3]=2[C:2]=1[C:36]1[CH:35]=[CH:34][C:33]([CH:29]([CH:30]([CH3:32])[CH3:31])[CH2:28][N:20]([CH3:19])[C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 674500069-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-oneHCID 86689457HCID 86689457, compound

Product 1

HCID 68226050tert-Butyl 2-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)-3-methylbutyl(methyl)carbamateYield 14%

Procedure

Following General Procedure B, 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one) (440 mg, 1.4 mmol) was reacted with tert-butyl methyl(3-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)carbamate (600 mg, 1.5 mmol) to afford the desired product (100 mg, 14%) as a yellow solid: ESI MS m/z 521 [C30H36N2O4S+H]+.

Sources & evidence

ORD record
ord-b48bb0eef4b64eb699170c9c6b021101
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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