Cesium carbonate → HCID 118480344, compound

HRID 1483176Notes

Reaction equation

HRID 1483176 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[CH:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].Br[C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][N:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].BrC1C=CC(N2CCOCC2=O)=NC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([CH:7]2[CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:3][C:2]2=[O:1])=[N:20][CH:21]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 693532,5-DibromopyridineHCID 84038454HCID 84038454, compoundHCID 118480346HCID 118480346, compound

Product 1

HCID 118480344HCID 118480344, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

3-oxopiperidin-1-benzyl formate (860 mg, 2.67 mmol), 2,5-dibromopyridine (949 mg, 4.01 mmol), cesium carbonate (1.74 g, 5.34 mmol), Pd2(dba)3 (127 mg, 0.13 mmol) and xantphos (92.3 mg, 0.16 mmol) reacted following the synthetic method of compound 19a to afford 1 g of white solid, yield 97%.

Sources & evidence

ORD record
ord-6d64eff9605e4326ab32b066d580a03f
Source dataset
uspto-grants-2016_08
Patent number
US09416144B2

Reaction notes

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