2-(2-(Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile → [2-(3-Methylamino-pyridin-4-yl)-phenyl]-acetonitrile

HRID 878199Notes

Reaction equation

HRID 878199 reaction equation
F[C:2]1[C:7](F)=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]([CH2:32]CS(C)(=O)=O)C(=O)C2C=C(C(F)(F)F)N=C(C(F)(F)F)C=2)=[C:4](OC)[CH:3]=1.CC1(C)C(C)(C)OB(C2C=CC=CC=2[CH2:54][C:55]#[N:56])O1>CCCCCCC.CCOC(C)=O>[CH3:32][NH:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[CH2:54][C:55]#[N:56]

Participants

4

Reactant 2

HCID 38328842-(2-(Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrileHCID 86670771N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-(2-methanesulfonyl-ethyl)-2,6-bis-trifluoromethyl-isonicotinamide2×

Product 1

HCID 70663360[2-(3-Methylamino-pyridin-4-yl)-phenyl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from (4-iodo-pyridin-3-yl)-methyl-amine (example 98, intermediate b) and [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetonitrile (CAS RN 325141-71-7) after a reaction time of 6 days and using a gradient of n-heptane:EtOAc (100:0 to 20:80) for the chromatographic purification. Light yellow solid (69%). MS (ESI): m/z=224.118 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-e6effa0852f94d3ea35d9dcecc66d09b
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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