Triethylamine → HCID 86695409, compound

HRID 525522Notes

Reaction equation

HRID 525522 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1.[CH2:10]([S:12](Cl)(=[O:14])=[O:13])[CH3:11].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][S:12]([CH2:10][CH3:11])(=[O:14])=[O:13])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 49761678(5-Bromopyridin-2-yl)methanamine

Product 1

HCID 86695409HCID 86695409, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromopyridin-2-yl)methanamine (250 mg, 1.34 mmol) in CH2Cl2 (3 mL) is added ethyl sulfonyl chloride (95 mg, 0.74 mmol) followed by triethylamine (0.3 mL, 2.0 mmol). The reaction is stirred at room temperature for 1.5 hours. The reaction is directly injected onto a 12 g silica gel column and chromatographed eluting from 100% hexanes to 50:50 ethylacetate:hexanes to afford the title compound (158 mg): m/z (Cl) M+H 279+281.

Workup

  1. customchromatographed
  2. washeluting from 100% hexanes to 50:50 ethylacetate

Sources & evidence

ORD record
ord-13fbdc909c21455bbbb4579a605f2ccb
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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