Cesium carbonate → HCID 59754790, compound

HRID 1713419Notes

Reaction equation

[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([OH:16])[CH:15]=[C:10]3[CH:9]=[C:8]2[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][CH:3]=1.Cl.Cl[CH2:28][C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([O:16][CH2:28][C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:30]=4)[CH:15]=[C:10]3[CH:9]=[C:8]2[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of the aforementioned Ethyl 3-[1-(4-chloro-benzyl)-5-hydroxy-1H-pyrrolo[2,3-b]pyridin-2-yl]-propionate (68 mg, 0.190 mmol) in DMF (1 mL) was added 2-chloromethylquinoline hydrochloride (49 mg, 0.228 mmol), cesium carbonate (124 mg, 0.380 mmol) and catalytic TBAI. The mixture was then heated to 55° C. for 12 hours after which it was partitioned between EtOAc and water, the aqueous layer extracted with EtOAc, the combined organic phases dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on silica gel eluting with a gradient of 0 to 30% EtOAc in hexanes to afford the title ester.

Workup

customwas partitioned between EtOAc and water
extractionthe aqueous layer extracted with EtOAc
dry with materialthe combined organic phases dried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe residue was purified on silica gel eluting with a gradient of 0 to 30% EtOAc in hexanes

Sources & evidence

ORD record: ord-558a7320efef4d1ebd85fba36b020d9e
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795274B2

Reaction notes

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