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. Author manuscript; available in PMC: 2013 Dec 2.
Published in final edited form as: Tetrahedron. 2012 Dec 2;68(48):10049–10058. doi: 10.1016/j.tet.2012.08.044

Table 3.

Synthesis of N-acyl indole(cyclo)alkanoic acids

graphic file with name nihms413885u3.jpg
# Y R1 R2 R3 R4 method yield (%)a
2 C OMe CH2C(O)OH H p-Cl D 81
22a C OMe CH2C(O)OH Me p-F D 90
22b C OMe CH2C(O)OH Me m-CF3 D 97
22c C OMe CH2C(O)OH Me p-CF3 D 90
22d C OMe CH2C(O)OH Me p-Me D 82
22e C OMe CH2C(O)OH Me p-CH2Cl D 98
22f C OMe CH2C(O)OH Me p-OMe D 93*
22g C OMe CH2C(O)OH H p-F D 76
22h C OMe CH2C(O)OH H m-CF3 D 96
22i C OMe CH2C(O)OH H p-CF3 D 99
22j C OMe CH2C(O)OH H graphic file with name nihms413885t7.jpg D 94
22k C F CH2C(O)OH Me p-Cl D 87
22l C F CH2C(O)OH Me m-CF3 D 95
22m C F CH2CH2C(O)OH Me p-Cl D 95
22n C F CH2C(O)OH H p-Cl D 78
23 C OMe graphic file with name nihms413885t8.jpg m-CF3 D 98*
24 N OMe CH2C(O)OH --- Cl D No product (decomposition)

Reagents and Conditions: [method D]: trimethyltin hydroxide, 1,2-DCE, microwave, 130 °C, 30 min.

a

isolated yield;

*

crude educts used; impurity of the starting material taken into account for the calculation of the percent yield (see Supporting Information)!