18-Crown-6 → 4-Chloro-2-cyclohexyl-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8]C(=O)OC(C)(C)C)[C:3]=1[C:16]#[C:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:17]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:16][C:3]=12Participants
5
Conditions
- Temperature
- 85 °C
Procedure
A solution of Example 98A (870 mg, 2.60 mmol) in 20 mL toluene was treated with potassium tert-butoxide (729 mg, 6.50 mmol) and 18-crown-6 (68.7 mg, 0.260 mmol) and the mixture was heated at 65° C. for 6 hours and at 85° C. overnight. The cooled mixture was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate (twice). The combined organic extracts were rinsed with water (once) and brine (twice), dried over magnesium sulfate, filtered, and concentrated. The residue was suspended in diethyl ether and the solids were collected and rinsed with diethyl ether to afford the title compound. MS (DCI) m/e 235/237 (M+H)+.
Workup
- customThe cooled mixture was partitioned between ethyl acetate and water
- customThe layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate (twice)
- washThe combined organic extracts were rinsed with water (once) and brine (twice),
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customthe solids were collected
- washrinsed with diethyl ether
Sources & evidence
- ORD record
- ord-4aa94d19f7e94ac5bf3b63b532a6172f
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073922B2
Reaction notes
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