(3-Bromopropoxy)(tert-butyl)dimethylsilane → HCID 57744477, compound

HRID 1887318Notes

Reaction equation

HRID 1887318 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[F:13][C:14]1[CH:15]=[C:16]([CH:35]=[CH:36][CH:37]=1)[CH2:17][NH:18][C:19]([C:21]1[S:22][C:23]([N:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][C:28]2=[O:34])=[CH:24][C:25]=1[CH3:26])=[O:20]>>[Si:6]([O:5][CH2:4][CH2:3][CH2:2][O:33][C:30]1[CH:31]=[CH:32][N:27]([C:23]2[S:22][C:21]([C:19]([NH:18][CH2:17][C:16]3[CH:35]=[CH:36][CH:37]=[C:14]([F:13])[CH:15]=3)=[O:20])=[C:25]([CH3:26])[CH:24]=2)[C:28](=[O:34])[CH:29]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 57744452HCID 57744452, compound

Product 1

HCID 57744477HCID 57744477, compound

Procedure

Following the procedure as described in Example 9, making variations only as required to use (3-bromopropoxy)(tert-butyl)dimethylsilane in place of 2-cyclopropylethyl 4-methylbenzenesulfonate to react with N-(3-fluorobenzyl)-5-(4-hydroxy-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide, the title compound was obtained as a yellowish viscous oil in quantitative yield: 1H NMR (300 MHz, CDCl3) δ 7.54 (d, J=7.8 Hz, 1H), 7.35-7.27 (m, 1H), 7.12 (d, J=7.8 Hz, 1H), 7.05 (d, J=9.6 Hz, 1H), 7.00-6.94 (m, 1H), 6.85 (s, 1H), 6.19 (t, J=5.8 Hz, 1H), 6.07 (dd, J=7.8, 2.7 Hz, 1H), 5.98 (d, J=2.7 Hz, 1H), 4.59 (d, J=5.8 Hz, 2H), 4.07 (t, J=6.0 Hz, 2H), 3.77 (t, J=6.0 Hz, 2H), 3.52 (t, J=6.0 Hz, 2H), 2.54 (s, 3H), 0.88 (s, 9H), 0.04 (s, 6H); MS (ES+) m/z 531.5 (M+1).

Sources & evidence

ORD record
ord-c1cf27469c2e4446bf058654f7f81be8
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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