5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → HCID 68153473, compound

HRID 1946931Notes

Reaction equation

HRID 1946931 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=2)([CH3:14])[N:13]=1)([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:31]2[CH:32]=[N:33][CH:34]=[C:35]([CH:38]=2)[C:36]#[N:37])O1>[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:31]3[CH:32]=[N:33][CH:34]=[C:35]([C:36]#[N:37])[CH:38]=3)[CH:16]=2)([CH3:14])[N:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 164142165-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrileHCID 66666279HCID 66666279, compound

Product 1

HCID 68153473HCID 68153473, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

In a manner analogous to that described for the preparation of Example 1, the palladium-catalyzed coupling of (RS)-[5-(3-bromo-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester (intermediate XIII-1) with 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinonitrile using [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) as the catalyst yielded the title compounds as a white semisolid. MS (ISP): m/z=393.2 [M+H]+.

Workup

  1. customIn a manner analogous to that described for the preparation of Example 1

Sources & evidence

ORD record
ord-78da7533fb0943d98c802c7ac8c59698
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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