Binap, (A+-)- → HCID 72705994, compound

HRID 577431Notes

Reaction equation

HRID 577431 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[N:10]=[N:11][C:12]([C:22]([NH2:24])=[O:23])=[C:13]([NH:15][C:16]2[CH:17]=NC=[CH:20][CH:21]=2)[N:14]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.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.IC1C=C[N:117]=[C:116]2[N:120]([CH3:123])[N:121]=[CH:122]C=12>CC([O-])=O.CC([O-])=O.[Pd+2].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].O1CCOCC1>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[N:10]=[N:11][C:12]([C:22]([NH2:24])=[O:23])=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][N:117]=[C:116]3[N:120]([CH3:123])[N:121]=[CH:122][C:17]=23)[N:14]=1

Participants

8

Reactant 4

HCID 634876Binap, (A+-)-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67548813HCID 67548813, compoundHCID 72705803HCID 72705803, compound

Product 1

HCID 72705994HCID 72705994, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared in the same procedure as described in Example 3-(((1R,2S)-2-aminocyclohexyl)amino)-5-(pyridin-3-ylamino)-1,2,4-triazine-6-carboxamide. However, here Pd(OAc)2 and BINAP were substituted for Pd2(dba)3 and Xantphos. Additionally, dioxane was used as the solvent. The coupling partner, 4-iodo-1-methyl-1H-pyrazolo[3,4-b]pyridine, was synthesized as seen below.

Sources & evidence

ORD record
ord-a330a4137b5a4f93b27d0714c75cf61b
Source dataset
uspto-grants-2015_05
Patent number
US09040530B2

Reaction notes

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