Diisopropylethylamine → HCID 11472787, compound

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 3-ethyl-5-formyl-4-iodo-1H-pyrrole-2-carboxylate was obtained following the procedures described in Example 1. Pd(Pt-Bu3)2 (7.0 mg, 0.010 mmol), Pd2(dba)3 (6.0 mg, 0.010 mmol), and CuI (2.0 mg, 0.010 mmol) were combined in a dry flask under N2 prior to evacuating the flask and refilling with argon. After the flask was charged with dioxane (2.0 mL) it was sparged with argon prior to the sequential addition of i-Pr2NEt (0.0259 mL, 0.19 mmol), a solution of tert-butyl 3-ethyl-5-formyl-4-iodo-1H-pyrrole-2-carboxylate (56.0 mg, 0.16 mmol) in dioxane (1.0 mL), and 2-ethynylpyridine (0.0194 mL, 0.19 mmol). The reaction was heated to 80° C. until complete consumption of the starting material. After the reaction was cooled to ambient temperature, it was filtered through a plug of silica gel and concentrated in vacuo. The resultant residue was dissolved in acetonitrile and purified by reverse phase HPLC. Proton NMR for the product was consistent with the title compound. 1H NMR (500 MHz, CDCl3) δ 10.23 (s, 1H); 3.10 (q, J=7.3 Hz, 2H); 1.61 (s, 9H); 1.16 (t, J=7.3 Hz, 3H). HRMS (ES) exact mass calculated for C21H21F3N2O5 (M+H+): 325.1547. Found 325.1549.

Provenance & Evidence