Dichloromethane → HCID 71104923, compound

HRID 1897591Notes

Reaction equation

HRID 1897591 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][C:4]=1[F:12])#[N:2].Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[CH:20]([OH:22])[CH3:21].C(Cl)Cl>CN(C=O)C.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]>[F:12][C:4]1[CH:5]=[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][C:19]=2[CH:20]([OH:22])[CH3:21])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 2783130(4-Cyano-3-fluorophenyl)boronic acidHCID 667978531-(3-Bromopyridin-4-yl)ethanol

Product 1

HCID 71104923HCID 71104923, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To the solution of 4-cyano-3-fluoro phenylboronic acid (247 mg, 1.50 mmol), 1-(3-Bromo-pyridin-4-yl)-ethanol (303 mg, 1.50 mmol) and PdCl2(dppf). CH2Cl2 adduct (98 mg, 0.12 mmol) in DMF (6 mL) was added 2M Na2CO3aq (1.50 ml, 3.00 mmol) under Nitrogen atmosphere. The mixture was stirred and heated at 100° C. for 4 hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and saturated NH4Cl solution. After extraction with DCM and separation, the combined extracts were concentrated and purified by ISCO 12 g (10% MeOH/DCM=0-25%) to give 2-Fluoro-4-[4-(1-hydroxy-ethyl)-pyridin-3-yl]-benzonitrile (190 mg, 52%) as colorless solid; ESI-MS m/z: 243 [M+1]+, Retention time 1.05 min

Workup

  1. temperatureAfter letting cool to room temperature
  2. customsolvent was removed in vacuo
  3. dissolutionThe resulting residue was dissolved in DCM
  4. extractionAfter extraction
  5. customwith DCM and separation
  6. concentrationthe combined extracts were concentrated
  7. custompurified by ISCO 12 g (10% MeOH/DCM=0-25%)

Sources & evidence

ORD record
ord-ec31edd613dd426cac6a14377ece56ed
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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