Water → HCID 66786963, compound

HRID 1947459Notes

Reaction equation

C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][C:15]1[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=1)[CH:8]=2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.CCOC(C)=O>C1COCC1>[S:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[O:14][C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:5]([CH2:3][OH:2])[NH:6]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.) solution of 6-(benzothiazol-2-yloxy)-1H-indole-2-carboxylic acid methyl ester (200 mg, 0.61 mmol) in THF (6 mL) was added LAH (2 M in THF, 0.34 mL, 0.31 g, 0.68 mmol) and the reaction mixture was stirred (−78° C., 1 h). The reaction mixture was treated with H2O (5 mL) and EtOAc (10 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×25 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH (0.2 M NH3):DCM (0-4%) to provide the title compound as a beige solid (97 mg, 53%). MS (ESI): mass calcd. for C16H12N2O2S, 296.1; m/z found, 297.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.63 (s, 1H), 7.72 (d, J=8.1, 1H), 7.64 (dd, J=8.0, 0.7, 1H), 7.57 (d, J=8.5, 1H), 7.41-7.31 (m, 2H), 7.27-7.21 (m, 1H), 7.07 (dd, J=8.5, 2.2, 1H), 6.39 (s, 1H), 4.80 (d, J=5.9, 2H), 1.87 (t, J=5.9, 1H).

Workup

customThe organic layer was separated
extractionthe aqueous layer was extracted with EtOAc (2×25 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-85d3929986234b74aff94c582d05610f
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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