Sodium Carbonate → HCID 86680632, compound

HRID 1497467Notes

Reaction equation

HRID 1497467 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][CH:17]=[CH:16][C:15]=1B(O)O)#[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:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:12]#[N:13])=[CH:3][CH:4]=1)[CH2:9][CH3:10]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27346102-Cyanophenylboronic acidHCID 69679626HCID 69679626, compound

Product 1

HCID 86680632HCID 86680632, compoundYield 19.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-(5-bromopyridin-2-yl)propan-1-ol (0.7 g, 3.2 mmol) in toluene (15 mL) and ethanol (8 mL) was added 2-cyano phenyl boronic acid (0.57 g, 3.8 mmol) and a 2M solution of aq. Na2CO3. The reaction mixture was degassed with argon, Pd(PPh3)4 (0.187 g, 0.162 mmol) was added, the reaction mixture was again degassed with argon for 10 min, and the reaction heated to 100° C. for 3 h. The reaction mixture was evaporated under vacuum to remove ethanol, diluted with water (40 mL), extracted with ethyl acetate (200 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 20% ethyl acetate and hexane) to give 2-(6-(1-hydroxypropyl)pyridin-3-yl)benzonitrile. (0.150 g, 19.4% yield). 1H NMR (400 MHz DMSO-d6): δ 8.67 (s, 1H), 8.02-7.97 (m, 2H), 7.82 (t, 1H), 7.69 (d, 1H), 7.63-7.60 (m, 2H), 1.83-1.68 (m, 2H), 0.89 (t, 3H): LC-MS m/z calcd for [M+H]+ 239.11. found 239.0.

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. additiondiluted with water (40 mL)
  6. extractionextracted with ethyl acetate (200 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 20% ethyl acetate and hexane)

Sources & evidence

ORD record
ord-2626edc64135447cbb4b9dbed7475e5c
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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