Diisopropylamine → 3-[1,1′-Biphenyl]-3-yl-5,6-dimethoxy-2-pyridinecarbonitrile

HRID 625958Notes

Reaction equation

HRID 625958 reaction equation
Br[C:2]1[C:3]([C:12]#[N:13])=[N:4][C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1.[C:14]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.[Na+].O.S(C1C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=CC=1)([O-])(=O)=O.[Na+].[Na+].C(NC(C)C)(C)C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[C:14]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:19]=[CH:18][CH:17]=[C:16]([C:2]2[C:3]([C:12]#[N:13])=[N:4][C:5]([O:10][CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=2)[CH:15]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 2734315(3-Phenylphenyl)boronic acidHCID 53487040Sodium 3,3',3''-phosphinetriyltribenzenesulfonate hydrateHCID 67406660HCID 67406660, compound

Product 1

HCID 674080083-[1,1′-Biphenyl]-3-yl-5,6-dimethoxy-2-pyridinecarbonitrileYield 89%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 3-bromo-5,6-dimethoxypyridine-2-carbonitrile (31 mg, 0.128 mmol), 3-biphenylboronic acid (30 mg, 0.153 mmol), Pd(OAc)2 (5.7 mg, 0.026 mmol) and tris(3-sulfonatophenyl)phosphine hydrate sodium salt (49 mg, 0.077 mmol) in DMF (1 mL), under argon, were added diisopropylamine (0.045 mL, 0.319 mmol) and H2O (0.25 mL). Stirred at 65° C. for 5 h. Purification by preparative HPLC (10-75% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 36 mg (89%) of 3-(biphenyl-3-yl)-5,6-dimethoxypyridine-2-carbonitrile as a white solid. LC/MS (M+H)+ 317.1.

Workup

  1. customPurification
  2. additionby preparative HPLC (10-75% CH3CN/H2O over 20 min, 0.05% added TFA)

Sources & evidence

ORD record
ord-ed8dfbdb76f3496da6bbe7451078a995
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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