Tetrahydrofuran → HCID 90118026, compound

HRID 523152Notes

Reaction equation

HRID 523152 reaction equation
Cl[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][N:3]=1.[Br-].[S:10]1[CH:14]=[CH:13][N:12]=[C:11]1[Zn+].C1COCC1>CCOC(C)=O.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:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:11]2[S:10][CH:14]=[CH:13][N:12]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 27827922-Chloro-4-fluoropyridineHCID 178419763HCID 178419763, compound

Product 1

HCID 90118026HCID 90118026, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 2 dram vial equipped with a stir bar was added 2-chloro-4-fluoropyridine (99 mg, 0.75 mmol) and Pd(dppf)Cl2 (27 mg, 0.038 mmol). The vial was sealed with a septum screwcap and then was placed under N2 atmosphere. To the vial was added thiazol-2-ylzinc(II) bromide in THF (3.0 mL, 1.5 mmol). The vial was placed in a 60° C. heating block with stirring for 3.5 h. The reaction solution was transferred to a 125 mL reparatory funnel and was diluted with EtOAc (50 mL). The solution was washed with water:brine (25 mL:25 mL); then brine (50 mL). The organic solution was dried over MgSO4; filtered; then concentrated in vacuo. The resulting residue was subjected to silica gel chromatography (hexanes:EtOAc) to afford 2-(4-fluoropyridin-2-yl)thiazole as a white solid (106 mg, 78%). 1H-NMR (400 MHz, CDCl3-d) δ 8.59 (dd, J=8.3, 5.5 Hz, 1H), 7.98-7.92 (m, 2H), 7.49 (d, J=3.3 Hz, 1H), 7.07 (ddd, J=8.2, 5.6, 2.5 Hz, 1H): MS: MS m/z 181.0 (M++1).

Workup

  1. customTo a 2 dram vial equipped with a stir bar
  2. customThe vial was sealed with a septum screwcap
  3. customwas placed in a 60° C.
  4. temperatureheating block
  5. customThe reaction solution was transferred to a 125 mL reparatory funnel
  6. washThe solution was washed with water
  7. dry with materialThe organic solution was dried over MgSO4
  8. filtrationfiltered
  9. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-1d45df54c21f4efb8fed1820e24d7438
Source dataset
uspto-grants-2016_05
Patent number
US09334279B2

Reaction notes

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