Diethyl Ether → 2-[4-(2-Bromoethoxy)phenoxy][1,3]thiazolo[4,5-b]pyridine

HRID 547340Notes

Reaction equation

HRID 547340 reaction equation
Cl.Cl[C:3]1[S:4][C:5]2[C:6]([N:11]=1)=[N:7][CH:8]=[CH:9][CH:10]=2.[Br:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].C(OCC)C>CC#N>[Br:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:3]2[S:4][C:5]3[C:6]([N:11]=2)=[N:7][CH:8]=[CH:9][CH:10]=3)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 128339324-(2-Bromoethoxy)phenolHCID 574827652-Chlorothiazolo[4,5-b]pyridine hydrochloride

Product 1

HCID 574483802-[4-(2-Bromoethoxy)phenoxy][1,3]thiazolo[4,5-b]pyridineYield 87.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro[1,3]thiazolo[4,5-b]pyridine hydrochloride (863 mg, 4.17 mmol), 4-(2-bromo-ethoxy)-phenol (905 mg, 4.17 mmol), and Cs2CO3 (5.88 g, 16.67 mmol) was stirred in CH3CN (42 mL) for 16 h. After filtration through diatomaceous earth, the organic filtrate was partitioned with 1 M NaOH (3×10 mL) and satd. aq. NaCl (1×10 mL). The organic layer was dried and concentrated to yield a red oil. Additional desiccation under high vacuum yielded a brown solid in red oil. Diethyl ether was added, and the mixture was sonicated for 20 min to give a homogenous suspension. The pink solid was filtered and discarded, and the ether solution was concentrated to yield the title compound as a yellow solid (1.28 g, 87%). 1H NMR (500 MHz, CDCl3): 8.58 (dd, J=4.8, 1.7, 1H), 8.02 (dd, J=7.9, 1.67 1H), 7.38-7.34 (m, 2H), 7.21 (dd, J=7.9, 4.8, 1H), 7.01-6.97 (m, 2H), 4.33 (t, J=6.2, 2H), 3.68 (t, J=6.2, 2H). MS (ESI): mass calcd. for C14H11BrN2O2S, 349.97; m/z found, 351.0 [M+H]+.

Workup

  1. filtrationAfter filtration through diatomaceous earth
  2. customthe organic filtrate was partitioned with 1 M NaOH (3×10 mL)
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto yield a red oil
  6. customAdditional desiccation under high vacuum yielded a brown solid in red oil
  7. customthe mixture was sonicated for 20 min
  8. customto give a homogenous suspension
  9. filtrationThe pink solid was filtered
  10. concentrationthe ether solution was concentrated

Sources & evidence

ORD record
ord-4401c31b6ade4c088bda2b3f1a3f1e7c
Source dataset
uspto-grants-2011_05
Patent number
US07939527B2

Reaction notes

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