Lithium iodide → HCID 9910168, compound

HRID 413803Notes

Reaction equation

[I-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([O:19][CH2:20][C:21](=[O:23])[NH2:22])[C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:24]([O:26]C)=[O:25]>N1C=CC=CC=1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([O:19][CH2:20][C:21](=[O:23])[NH2:22])[C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:24]([OH:26])=[O:25]

Participants

Conditions

Temperature: 115 °C

Procedure

Lithium iodide (0.39 g) was added to stirred solution of methyl N-(3,4-dichlorobenzyl)-5-methoxy-4-carbamoylmethoxyindole-2-carboxylate (0.12 g) in pyridine (10 ml) under an atmosphere of argon. The reaction was then heated at 115° C. for 16 hours. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and hydrochloric acid (2.0 M, 10 ml). Combined organic extracts were washed with water and saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated in vacuo to give the product as a cream coloured solid (35 mg, 30%); NMR d (CD3SOCD3) 3.80 (s, 3H), 4.51 (s, 2H), 5.79 (s, 2H), 6.90 (dd, 1H), 7.18 (d, 1H), 7.25 (d, 1H), 7.34 (d, 1H), 7.39 (s, 1H), 7.42 (brs, 1H), 7.51 (d, 1H), 7.57 (brs, 1H), 13.05 (brs, 1H); M/z (−) 421 (M−H+).

Workup

customThe solvent was removed in vacuo
customthe residue was partitioned between ethyl acetate and hydrochloric acid (2.0 M, 10 ml)
washCombined organic extracts were washed with water and saturated aqueous sodium chloride solution
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9406cb882738466089d5528e5ae6f2d4
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06569888B1

Reaction notes

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