Chloroform → 7-Hydroxy-2-(6-phenylsulfanyl-pyridin-3-yl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642398Notes

Reaction equation

HRID 642398 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2].C(N(CC)CC)C.C(Cl)(Cl)Cl.[C:34]1([SH:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18]([S:40][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 7969ThiophenolHCID 8471TriethylamineHCID 866173622-(6-Chloro-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Product 1

HCID 684263487-Hydroxy-2-(6-phenylsulfanyl-pyridin-3-yl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Conditions

Temperature
100 °C

Procedure

A suspension of 2-(6-chloro-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester, example 92(c)(0.25 g, 0.75 mmol) and triethylamine (0.21 mL, 1.49 mmol) in thiophenol was heated at 100° C. overnight. 100 mL of chloroform was added. The organic solution was washed with saturated sodium bicarbonate solution and brine, dried, filtered, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes to produce 49.0 mg of a light yellow solid. MS: (+) m/z 410.3 (M+1).

Workup

  1. washThe organic solution was washed with saturated sodium bicarbonate solution and brine
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography
  6. washeluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-07c84e336c8a48abb1f3be0eef87f2e3
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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