Sodium Carbonate → HCID 86680629, compound

HRID 1497464Notes

Reaction equation

HRID 1497464 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:11])[CH2:9][CH3:10])=[N:6][CH:7]=1.[C:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)#[N:13].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:11][CH:8]([C:5]1[N:6]=[CH:7][C:2]([C:17]2[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)=[CH:3][CH:4]=1)[CH2:9][CH3:10]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 69679626HCID 69679626, compound

Product 1

HCID 86680629HCID 86680629, compoundYield 45.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-(5-bromopyridin-2-yl)propan-1-ol (0.3 g, 1.38 mmol) in toluene (8 mL) and ethanol (4 mL) was added 4-cyano phenyl boronic acid (0.244 g, 1.6 mmol) and a 2 M solution of aq. Na2CO3. The reaction mixture degassed with argon, Pd(PPh3)4 (0.08 g, 0.069 mmol) was added, the reaction mixture was again degassed with argon for 10 min, and heated to 80° C. for 4 h. The reaction mixture was evaporated under vacuum to remove ethanol, the reaction mixture was diluted with water (10 mL), extracted with ethyl acetate (100 mL), dried over sodium sulphate, filtered and evaporated under reduced pressure to obtain crude product. The crude product was purified by a Biotage Isolera® One column (using 15% ethyl acetate and hexane) to give 4-(6-(1-hydroxypropyl)pyridin-3-yl)benzonitrile (0.15 g, 45.45% yield). 1H NMR (400 MHz DMSO-d6): δ 8.78 (s, 1H), 7.89 (dd, 1H), 7.78 (d, 2H); 7.69 (d, 2H), 7.39 (d, 1H), 4.77 (t, 1H), 3.90 (s, 1H), 1.91-1.81 (m, 2H), 0.99 (t, 3H).

Workup

  1. additionwas added
  2. customthe reaction mixture was again degassed with argon for 10 min
  3. customThe reaction mixture was evaporated under vacuum
  4. customto remove ethanol
  5. additionthe reaction mixture was diluted with water (10 mL)
  6. extractionextracted with ethyl acetate (100 mL)
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto obtain crude product
  11. customThe crude product was purified by a Biotage Isolera® One column (using 15% ethyl acetate and hexane)

Sources & evidence

ORD record
ord-7baf7827256947398e38d5fffec8a4f6
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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