Water → HCID 68770101, compound

HRID 1947464Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]([CH2:25][CH3:26])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][C:16]1[S:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=1)=[CH:10][CH:9]=2)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[S:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[O:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:25][CH3:26])[C:6]([CH2:4][OH:3])=[CH:14]2

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.) solution of [5-(benzothiazol-2-yloxy)-1-ethyl-1H-indole-2-carboxylic acid ethyl ester (1.05 g, 3.1 mmol) in THF (30 mL) was added LAH (1 M in THF, 0.8 mL, 0.72 g, 7.8 mmol) and the reaction mixture was stirred (−78° C., 1 h) and allowed to warm (rt, 12 h). The reaction mixture was treated with H2O (10 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3×30 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH:DCM (5-15%) to provide the title compound as a colorless foam (0.5 g, 49%). MS (ESI): mass calcd. for C18H16N2O2S, 324.0; m/z found, 325.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 7.85 (d, J=7.2, 1H), 7.68 (d, J=7.6, 1H), 7.56 (s, 1H), 7.55 (d, J=6.4, 1H), 7.45-7.37 (m, 1H), 7.32-7.25 (m, 1H), 7.16 (dd, J=8.8, 2.4, 1H), 6.44 (s, 1H), 5.32 (s, 1H), 4.67 (s, 2H), 4.29 (q, J=7.1, 2H), 1.33 (t, J=7.1, 3H).

Workup

temperatureto warm (rt, 12 h)
customThe organic layer was separated
extractionthe aqueous layer was extracted with EtOAc (3×30 mL)
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-4ac9afc500bd4c348ef8f54b2e13c93b
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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