Ethyl 7-bromo-1H-indole-2-carboxylate

The mixture of General procedure: A mixture of lactam(1.0 eq), bromide(2.0 eq), Cul(0.5 eq), (trans)-1, 2-N, Ndimethylaminocyclohexane(1.0 eq), and K2C03(2.5 eq) in toluene(1 mL) was sparged withArgas for 5 min. The reaction mixture was sealed and heated to 110 C for 18 h. Same workup and purification protocols described in general coupling procedure A were followed toobtaine a desire product.i) Preparation of ethyl 7-cyclopropyl- 1 H-indole-2-carboxylate (1220) [00217] A mixture of ethyl 7-bromo-1 H-indole-2-carboxylate (300 mg, 1 .12 mmol), cyclopropylboronic acid (192.23 mg, 2.24 mmol), 2M Na2C03 (2.8 ml) and Pd(dppf)CI2 (40.94 mg, 0.06 mmol) in dioxane (9.7 mL) was purged with argon then subjected to microwave irradiation at 100 C for 2 h. The resulting mixture was filtered over celite, rinsing with EtOAc and water. The filtrate was partitioned between EtOAc and 1 M HCI. The aqueous phase was extracted with EtOAc and the combined organic extracts washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue was taken up in DCM, adsorbed onto silica and purified by flash chromatography (Telos 12 g, EtOAc in heptane, 0- 15%) to give the title compound contaminated with an unknown related impurity. The material was used in the next step without further purification. ii) Preparation of ethyl 7-cyclopropyl-3-iodo- 1 H-indole-2-carboxylate

Molecular Weight:268.11
XLogP3:3.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:266.98949
Monoisotopic Mass:266.98949
Topological Polar Surface Area:42.1
Heavy Atom Count:15
Complexity:247
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes