Boric Acid → Methyl 2-(2,3'-dicyano-4'-hydroxybiphenyl-4-yl)isonicotinate

HRID 1160826Notes

Reaction equation

HRID 1160826 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]([CH:28]=[CH:29][N:30]=3)[C:24]([O:26][CH3:27])=[O:25])=[CH:17][C:16]=2[C:31]#[N:32])=[CH:11][C:10]=1[C:33]#[N:34])C1C=CC=CC=1.B(O)(O)O.C(C1C=C(C2C=C(C=CN=2)C(OC)=O)C=CC=1OS(C(F)(F)F)(=O)=O)#N.[H][H]>C1COCC1.CO.[C].[Pd]>[C:31]([C:16]1[CH:17]=[C:18]([C:21]2[CH:22]=[C:23]([CH:28]=[CH:29][N:30]=2)[C:24]([O:26][CH3:27])=[O:25])[CH:19]=[CH:20][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([C:33]#[N:34])[CH:11]=1)#[N:32]

Participants

8

Reactant 4

HCID 7628Boric AcidHCID 66995426HCID 66995426, compoundHCID 86616562Methyl 2-(3-cyano-4-([(trifluoromethyl)sulfonyl]oxy)phenyl)isonicotinateHCID 178418361HCID 178418361, compound

Product 1

HCID 136407394Methyl 2-(2,3'-dicyano-4'-hydroxybiphenyl-4-yl)isonicotinateYield 47.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.32 g of methyl 2-[4′-(benzyloxy)-2,3′-dicyanobiphenyl-4-yl]isonicotinate, which had been obtained in the same manner as in Example 1(1) using 4-(benzyloxy)-3-cyanophenyl]boric acid and methyl 2-(3-cyano-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)isonicotinate, was dissolved in a mixture of 50 ml of THF and 50 ml of methanol, and 0.5 g of palladium-carbon was added, followed by stirring in a hydrogen atmosphere at room temperature for 12 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 0.5 g of methyl 2-(2,3′-dicyano-4′-hydroxybiphenyl-4-yl)isonicotinate.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b45cfd19bb044b21b25a77e3294476a9
Source dataset
uspto-grants-2010_10
Patent number
US07816558B2

Reaction notes

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