Cesium carbonate → HCID 90266380, compound

HRID 1483173Notes

Reaction equation

HRID 1483173 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C:23](=[O:25])[NH:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:27]1[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][N:28]=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:33][C:30]1[CH:31]=[CH:32][C:27]([N:22]2[CH2:21][C@@H:20]([CH2:19][O:18][Si:1]([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[O:24][C:23]2=[O:25])=[N:28][CH:29]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 693532,5-DibromopyridineHCID 84038454HCID 84038454, compoundHCID 86727233HCID 86727233, compound

Product 1

HCID 90266380HCID 90266380, compoundYield 70%

Reagents, catalysts & solvents 2

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

Procedure

Compound 25a (927 mg, 2.73 mmol), 2,5-dibromopyridine (500 mg, 2.1 mmol, cesium carbonate (1.03 g, 3.15 mmol), Pd2(dba)3 (100 mg, 0.1 mmol) and xantphos (73 mg, 0.13 mmol), reacted following the synthetic method of compound 19a to afford 750 mg of viscous liquid, yield 70%.

Sources & evidence

ORD record
ord-5d2ef78942984a5aa7592403f10a7197
Source dataset
uspto-grants-2016_08
Patent number
US09416144B2

Reaction notes

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