Cesium carbonate → HCID 57860544, compound

HRID 1947119Notes

Reaction equation

HRID 1947119 reaction equation
[F:1][CH:2]([F:32])[CH2:3][O:4][C:5]1[C:9]2[C:10](=[O:25])[N:11]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]([CH2:14][CH3:15])=[CH:13][C:8]=2[N:7]([CH3:26])[C:6]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28].FC(F)(F)S(OCC(F)F)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>>[F:32][CH:2]([F:1])[CH2:3][O:4][C:5]1[C:9]2[C:10](=[O:25])[N:11]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]([CH2:14][CH3:15])=[CH:13][C:8]=2[N:7]([CH3:26])[C:6]=1[C:27]([OH:29])=[O:28].[F:32][CH:2]([F:1])[CH2:3][O:4][C:5]1[C:9]2[C:10](=[O:25])[N:11]([CH2:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]([CH2:14][CH3:15])=[CH:13][C:8]=2[N:7]([CH3:26])[C:6]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 86634216HCID 86634216, compound

Product 2

HCID 57860544HCID 57860544, compoundYield 83%HCID 86634216HCID 86634216, compound

Procedure

In the same manner as in Reference Example 56, ethyl 3-(2,2-difluoroethoxy)-6-ethyl-1-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate was obtained from the compound of Reference Example 40 (500 mg, 1.31 mmol), 2,2-difluoroethyl trifluoromethanesulfonate (336 mg, 1.57 mmol) and cesium carbonate (554 mg, 1.70 mmol). The title compound (314 mg, 83%) was obtained as a white powder from the thus-obtained ethyl 3-(2,2-difluoroethoxy)-6-ethyl-1-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (400 mg, 0.90 mmol) by a method similar to that in Reference Example 59.

Sources & evidence

ORD record
ord-2be5a93cd84544a98862ade493bfef0f
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

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