1,3-Thiazol-2-ylmethanol → HCID 59354922, compound

HRID 1099445Notes

Reaction equation

HRID 1099445 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][N:3]=1.[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[CH2:18][OH:19]>>[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[CH2:18][O:19][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 27952131,3-Thiazol-2-ylmethanolHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 59354922HCID 59354922, compoundYield 21%

Conditions

Temperature
50 °C

Procedure

The title compound was synthesized as described for Intermediate example I-81 in 21% yield starting from ethyl 6-chloronicotinate and 1,3-thiazol-2-ylmethanol. The deprotonation step was performed at ambient temperature and the intermediate product was purified by column chromatography using a gradient of ethyl acetate in heptane. The reduction step was carried out in sodium hydroxide:ethanol 50/50 heated to 50° C. for 1.5 h; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.74 (d, 1 H), 8.21 (dd, 1 H), 7.83 (d, 1 H), 7.76 (d, 1 H), 7.04 (d, 1 H), 5.74 (s, 2 H); MS (APPI/APCI) m/z 237[M+H+].

Workup

  1. customwas performed at ambient temperature
  2. customthe intermediate product was purified by column chromatography

Sources & evidence

ORD record
ord-de60c25bc0f24e12b651e246fa5b13d5
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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