Dichloromethane → HCID 67405602, compound

HRID 625960Notes

Reaction equation

HRID 625960 reaction equation
Cl[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:12]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>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].C1COCC1>[C:12]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:17]=[CH:16][CH:15]=[C:14]([C:2]2[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[N:6][CH:7]=2)[CH:13]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2734315(3-Phenylphenyl)boronic acidHCID 224785605-Chloro-2,3-dimethoxypyridine

Product 1

HCID 67405602HCID 67405602, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 5-chloro-2,3-dimethoxypyridine (200 mg, 1.15 mmol), biphenyl-3-ylboronic acid (207 mg, 1.045 mmol), PdCl2(dppf).CH2Cl2 (43 mg, 0.052 mmol), under nitrogen, was added. THF (2.5 mL) followed by 1 M aqueous Na2CO3 solution (1.57 mL). The reaction mixture was heated at 150° C. (microwave irradiation) for 40 min, cooled to room temperature and partitioned between water and EtOAc. Layers were separated and the aqueous solution was extracted with EtOAc (2×). Combined organic solutions were dried over Na2SO4 and concentrated. Purification by flash chromatography (24 g silica gel, 1% to 20% EtOAc in hexanes) afforded 104 mg (34%) of 5-(biphenyl-3-yl)-2,3-dimethoxypyridine as a light yellow viscous liquid. LC/MS (M+H)+ 292.2.

Workup

  1. custom(microwave irradiation) for 40 min
  2. temperaturecooled to room temperature
  3. custompartitioned between water and EtOAc
  4. customLayers were separated
  5. extractionthe aqueous solution was extracted with EtOAc (2×)
  6. dry with materialCombined organic solutions were dried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by flash chromatography (24 g silica gel, 1% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e6e920864060480d99d8e48cf5a96b91
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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