HCID 12415565, compound → HCID 77230811, compound

HRID 409015Notes

Reaction equation

HRID 409015 reaction equation
[Br:1][C:2]1[S:13][C:5]2=[N:6][C:7]([Cl:12])=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=1.[CH3:14][Mg]Cl>C1COCC1>[Br:1][C:2]1[S:13][C:5]2=[N:6][C:7]([Cl:12])=[C:8]([CH:10]([OH:11])[CH3:14])[CH:9]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 12415565HCID 12415565, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 77230811HCID 77230811, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 2-bromo-6-chlorothieno[2,3-b]pyridine-5-carbaldehyde (2.4 g, 8.7 mmol) (Meth-Cohn, O. Narine B. Tetrahedron Lett., 1978, 2045) in THF (50 mL) at −20° C. was added methylmagnesiumchloride (3.04 mL of 3N in THF, 9.1 mmol) dropwise. The reaction was stirred at −20° C. for 45 minutes and then quenched with 25 mL NH4Cl (sat) and 25 mL of water. The reaction was diluted with ether and the layers were separated. The organic layer was washed with brine and concentrated. Purification by column chromatography afforded 1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethanol. LC/MS (M+1, found=293.8). 1H NMR (400 MHz, CDCl3) δ 8.21 (s, 1H), 7.30 (s, 1H), 5.32 (qd, J=6.3, 2.7 Hz, 1H), 2.19 (br s, 1H), 1.55 (d, J=6.3 Hz, 3H) ppm.

Workup

  1. customquenched with 25 mL NH4Cl (sat) and 25 mL of water
  2. additionThe reaction was diluted with ether
  3. customthe layers were separated
  4. washThe organic layer was washed with brine
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-5d49e94963b842c59125bc6c03c07f2f
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

Loading…