HCID 67406794, compound → HCID 67406460, compound

HRID 625955Notes

Reaction equation

HRID 625955 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:12](Br)=[CH:11][C:10]([O:14][CH3:15])=[C:9]([O:16][CH3:17])[N:8]=2)[CH:2]=1.C1(C2C=CC=CC=2)C=CC=C(C2[C:31](Br)=[N:32]C(OC)=C(OC)C=2)C=1>[C-]#N.[C-]#N.[Zn+2].[Zn].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].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.[Fe+2].CC(N(C)C)=O>[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:12]([C:31]#[N:32])=[CH:11][C:10]([O:14][CH3:15])=[C:9]([O:16][CH3:17])[N:8]=2)[CH:2]=1

Participants

8

Reactant 2

HCID 67406794HCID 67406794, compoundHCID 86675488HCID 86675488, compound

Product 1

HCID 67406460HCID 67406460, compoundYield 39%

Reagents, catalysts & solvents 5

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

To the above mixture of 2-(biphenyl-3-yl)-3-bromo-5,6-dimethoxypyridine and 3-(biphenyl-3-yl)-2-bromo-5,6-dimethoxypyridine (50 mg, 0.135 mmol) were added, under argon, Zn(CN)2 (32 mg, 0.27 mmol), Zn powder (0.9 mg, 0.014 mmol), Pd2(dba)3 (12.4 mg, 0.014 mmol), DPPF (15 mg, 0.027 mmol), DMA (2 mL) and stirred at 120° C. for 3.5 h. Cooled to room temperature and filtered. Purification by preparative HPLC (10->85% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 17 mg (39%) of 2-(biphenyl-3-yl)-5,6-dimethoxypyridine-3-carbonitrile as a tan solid. LC/MS (M+H)+ 317.2.

Workup

  1. additionwere added, under argon
  2. filtrationfiltered
  3. customPurification
  4. additionby preparative HPLC (10->85% CH3CN/H2O over 20 min, 0.05% added TFA)

Sources & evidence

ORD record
ord-1508e887c46a4f24963ab4b446242ff2
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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