Ethyl Bromide → 2-Ethylthieno[2,3-b]pyridine

HRID 1265008

Reaction equation

HRID 1265008 reaction equation
[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[Li][C:11](C)(C)[CH3:12].BrCC>C1COCC1.CCOC(C)=O>[CH2:11]([C:2]1[S:1][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1)[CH3:12]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 289928Thieno(2,3-b)pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 120449142-Ethylthieno[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of thieno[2,3-b]pyridine (0.35 g, 2.6 mmoles) prepared according to well known methods [see, Klemm, et al. (1969) J. Org. Chem., 34:347-354; see, also U.S. Pat. Nos. 5,026,700, 4,577,014, 4,406,898, 4,375,544, 4,311,845, and 4,161,599] in THF (10 ml) at −78° C. was added t-BuLi (1.7 M, 2.0 ml, 3.4 mmoles). The reaction solution was slowly warmed to −30° C. over a 45 minute period followed by the addition of bromoethane (0.25 ml, 3.4 mmoles). The solution was stirred 2 hours at ambient temperature then diluted with EtOAc (50 ml) and washed with H2O (75 ml). The organic phase was dried (MgSO4), filtered and concentrated to collect 0.41 g (97%) of the title compound as an orange-brown oil.

Workup

  1. washwashed with H2O (75 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto collect 0.41 g (97%) of the title compound as an orange-brown oil

Sources & evidence

ORD record
ord-05afbdece0b44b8a8a5a3efc9ec8081e
Source dataset
uspto-grants-2003_04
Patent number
US06545014B2

Linked notes

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