Triethylamine → N-(7-Bromo-imidazo[1,2-a]pyridin-2-ylmethyl)-methane sulfonamide

HRID 1487488Notes

Reaction equation

HRID 1487488 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11][NH2:12])[N:10]=[C:4]2[CH:3]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11][NH:12][S:21]([CH3:20])(=[O:23])=[O:22])[N:10]=[C:4]2[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 72209893(7-Bromoimidazo[1,2-A]pyridin-2-YL)methanamine

Product 1

HCID 86695441N-(7-Bromo-imidazo[1,2-a]pyridin-2-ylmethyl)-methane sulfonamideYield 31.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of C-(7-Bromo-imidazo[1,2-a]pyridin-2-yl)-methylamine (310 mg, 1.371 mmol) in CH2Cl2 (5 mL) is added triethyl amine (0.23 mL), 1.64 mmol) followed by methane sulfonyl chloride (0.112 mL, 1.371 mmol) at 0° C. then stirred at room temperature for 2 hours. The reaction mixture is diluted with water and extracted with CH2Cl2. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography eluting in 2% methanol:CH2Cl2 to afford the title compound (130 mg). 1H-NMR (400 MHz, DMSO-d6) δ: 2.91 (s, 3H), 4.25 (d, J=6.08 Hz, 2H), 7.04-7.06 (dd, J1=1.88 Hz, J2=7.24 Hz, 1H), 7.58 (t, J=6.12 Hz, 1H), 7.81 (d, J=0.88 Hz, 1H), 7.89 (s, 1H), 8.51 (d, J=7.04 Hz, 1H). LC-MS (m/z): [M+H]=306.0.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialOrganic layer is dried over sodium sulphate, solvent
  3. customis evaporated in vacuo
  4. custompurified by column chromatography
  5. washeluting in 2% methanol

Sources & evidence

ORD record
ord-71c2fd3d2ce54e41ac676f442cc34cd3
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

Loading…