N-bromobutanimide → tert-Butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenyl)propylcarbamate

HRID 1853744Notes

Reaction equation

HRID 1853744 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[C:10]4[CH:23]=[CH:22][S:21][C:11]=4[C:12](=[O:20])[NH:13][C:14]=3[CH:15]=[CH:16][C:17]=2[O:18][CH3:19])[CH:5]=[CH:4][C:3]=1[CH:24]([CH3:34])[CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].C1C(=O)N([Br:42])C(=O)C1>>[Br:42][C:15]1[C:14]2[NH:13][C:12](=[O:20])[C:11]3[S:21][CH:22]=[CH:23][C:10]=3[C:9]=2[C:8]([C:6]2[CH:5]=[CH:4][C:3]([CH:24]([CH3:34])[CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[C:2]([F:1])[CH:7]=2)=[C:17]([O:18][CH3:19])[CH:16]=1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 67447222tert-Butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Product 1

HCID 67448905tert-Butyl 2-(4-(6-bromo-8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)-2-fluorophenyl)propylcarbamateYield 49.9%

Procedure

Following General Procedure I, tert-butyl 2-(2-fluoro-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (500 mg, 1.0 mmol) was reacted with NBS (220 mg, 1.2 mmol) to afford the desired product (280 mg, 48%) as a brown oil. ESI MS m/z 561 [C26H26BrFN2O4S+H]+.

Sources & evidence

ORD record
ord-96a9c01375a34578bab0d3b9c414f5f6
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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