Cesium carbonate → Methyl 2-[3-[2-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]acetylamino]piperidin-1-yl]benzoate

HRID 602160Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH2:12][CH2:11][CH2:10][CH:9]([NH:13][C:14](=[O:29])[CH2:15][C:16]2[S:20][C:19]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:18][C:17]=2[CH3:28])[CH2:8]1.I[C:31]1[CH:40]=[CH:39][CH:38]=[CH:37][C:32]=1[C:33]([O:35][CH3:36])=[O:34]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1(C)C=CC=CC=1>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([C:19]2[S:20][C:16]([CH2:15][C:14]([NH:13][CH:9]3[CH2:10][CH2:11][CH2:12][N:7]([C:31]4[CH:40]=[CH:39][CH:38]=[CH:37][C:32]=4[C:33]([O:35][CH3:36])=[O:34])[CH2:8]3)=[O:29])=[C:17]([CH3:28])[N:18]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In an argon atmosphere, tri(dibenzylideneacetone)dipalladium (4.85 mg, 0.00530 mmol), 1,1′-bis(diphenylphosphino)ferrocene (9.09 mg, 0.0159 mmol) and cesium carbonate (48.2 mg, 0.148 mmol) were added to a toluene solution (1 mL) containing N-(piperidin-3-yl)-2-[2-(4-chlorophenyl)-4-methylthiazol-5-yl]acetamide (37.2 mg, 0.106 mmol) and methyl 2-iodobenzoate (27.8 mg, 0.106 mmol). This reaction mixture was stirred at 100° C. for 8 hours. Subsequently, the mixture was allowed to cool and was filtered through Celite. The filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=2:1->1:1) to give 23.0 mg (45%) of the desired compound as a colorless oil.

Workup

temperatureto cool
filtrationwas filtered through Celite
customThe filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=2:1->1:1)

Sources & evidence

ORD record: ord-147dba057f4c4815b98988ca152a3f0e
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902367B2

Reaction notes

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