Bromine → (RS)-1-[2-(3-bromo-benzofuran-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanone

HRID 1367040Notes

Reaction equation

HRID 1367040 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[C:17]([C:19]1[N:20]=[C:21]([CH3:31])[S:22][C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:18].[Br:32]Br>C(OCC)C.ClCCl>[Br:32][C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][C:2]=1[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[C:17]([C:19]1[N:20]=[C:21]([CH3:31])[S:22][C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:18]

Participants

5

Reactant 2

HCID 24408BromineHCID 10160068(RS)-2-(2-Benzofuranylmethyl)-1-((5-(4-fluorophenyl)-2-methyl-thiazol-4-yl)-carbonyl)-piperidine

Product 1

HCID 23146338(RS)-1-[2-(3-bromo-benzofuran-2-ylmethyl)-piperidin-1-yl]-1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-methanoneYield 25%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To (RS)-2-(2-benzofuranylmethyl)-1-((5-(4-fluorophenyl)-2-methyl-thiazol-4-yl)-carbonyl)-piperidine, E1 (0.90 g, 2 mmol) in dry diethyl ether (10 ml) and dichloromethane (20 ml) cooled to −12° C. under argon, was added drop-wise a solution of bromine (0.36 g, 2 mmol) in dichloromethane (10 ml) over 0.5 h. The resulting solution was warmed to ambient temperature over 1.5 h, then stirred for a further 18 h. The reaction mixture was evaporated then re-evaporated from dichloromethane (3×). The resulting amorphous solid was chromatographed (silica gel with ethyl acetate-hexane mixtures) to afford the title compound as an amorphous solid (0.27 g, 25%).

Workup

  1. customThe reaction mixture was evaporated
  2. customthen re-evaporated from dichloromethane (3×)
  3. customThe resulting amorphous solid was chromatographed (silica gel with ethyl acetate-hexane mixtures)

Sources & evidence

ORD record
ord-c8950a19980d45d9877df8a65193720a
Source dataset
uspto-grants-2011_02
Patent number
US07893090B2

Reaction notes

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