Chlorosuccinimide → HCID 71284263, compound

HRID 1481760Notes

Reaction equation

[CH2:1]([O:8][C:9]1[N:18]=[C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[CH:23]=[CH:22]3)[C:16]([CH2:29][CH3:30])=[C:15]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Cl:46])C(=O)C1>CC#N>[CH2:1]([O:8][C:9]1[N:18]=[C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[CH:23]=[C:22]3[Cl:46])[C:16]([CH2:29][CH3:30])=[C:15]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2,4-bis(benzyloxy)-5-ethyl-6-(1-methyl-1H-indol-5-yl)nicotinate (131 mg, 0.26 mmol), prepared in Example 359, step 1, in MeCN (2 mL) was added NCS (35 mg, 0.26 mmol) at 0° C. The reaction was stirred at 0° C. for 1 h before it was allowed to warm to room temperature. The reaction progress was monitored by LC-MS. Upon completion, the reaction was quenched with water then extracted by CH2Cl2 (3×20 mL). The solvent was removed to give the crude product which was purified by flash column chromatography (0-10% EtOAc in hexanes) to afford the desired product (100 mg, 71%).

Workup

temperatureto warm to room temperature
customUpon completion, the reaction was quenched with water
extractionthen extracted by CH2Cl2 (3×20 mL)
customThe solvent was removed
customto give the crude product which
customwas purified by flash column chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-47e20a2ea4bd45ca9e5902c4bb71bc27
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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