Methyl 4-chloroacetoacetate → Methyl 2-(6,8-dibromoimidazo[1,2-a]pyridin-2-yl)acetate hydrochloride

HRID 1958488Notes

Reaction equation

HRID 1958488 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[Cl:10][CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH3:17])=[O:15]>C1COCC1>[ClH:10].[Br:8][C:6]1[CH:7]=[C:2]([Br:1])[C:3]2[N:4]([CH:11]=[C:12]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[N:9]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 36240Methyl 4-chloroacetoacetateHCID 988513,5-Dibromo-2-pyridylamine

Product 1

HCID 67008341Methyl 2-(6,8-dibromoimidazo[1,2-a]pyridin-2-yl)acetate hydrochlorideYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,5-dibromopyridin-2-amine (9.03 g, 35.8 mmol) and methyl 4-chloro-3-oxobutanoate (2.0 g, 13 mmol) in THF (50 mL) was heated at reflux 48 hrs. The solid was filtered and dried to give methyl 2-(6,8-dibromoimidazo[1,2-a]pyridin-2-yl)acetate hydrochloride (1.48 g, 36% yield). LCMS B: 1.54 min (RT); (M+H)+=347.07 (75%), 349.07 (100%), 351.04 (75%). 1H NMR, 400 MHz, CDCl3: δ 9.01 (d, 1.4 Hz, 1 H), 8.38 (s, 1 H), 8.07 (d, 1.4 Hz, 1 H), 4.25 (s, 2 H), 3.40 (s, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux 48 hrs
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-a441f8b5b8304894b1e582ac0394e40b
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

Loading…