Triethylamine → HCID 86695409, compound

HRID 1487455Notes

Reaction equation

HRID 1487455 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 (CI) M+H 279+281.

Workup

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

Sources & evidence

ORD record
ord-4148b4c0739c41c0a389080998f48966
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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