Water → HCID 16660039, compound

HRID 491025Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:17][CH:16]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[N:25]1([CH2:24][CH2:23][CH2:22][O:21][C:18]2[CH:17]=[CH:16][C:15]([N:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH:14]=[C:6]3[CH2:4][OH:3])=[CH:20][CH:19]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 60 °C

Procedure

(1-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]-1H-indole-2-carboxylic acid ethyl ester (0.5 g, 1.27 mmol) was dissolved in THF (10 mL) and added dropwise to lithium aluminum hydride (1.53 mL, 1 M solution in THF, 1.53 mmol) in THF (10 mL). The reaction was stirred at 60° C. for 2 hours. Water (0.3 mL), 2 N NaOH (0.3 mL), and water (0.9 mL) were added, and the solvent was evaporated. The resulting residue was diluted with water and extracted with dichloromethane. The dichloromethane extracts were dried over MgSO4 and concentrated to give a white solid, 0.36 g. A small amount of the product was purified by semi-prep LC-MS to give 3.5 mg of pure desired product. LC-MS (C22H26N2O2 calc'd 350) m/z 351 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.65-7.61 (m, 1H), 7.35 (d, J=8.7 Hz, 2H), 7.16-7.08 (m, 3H), 7.01 (d, J=8.7 Hz, 2H), 6.65 (s, 1H), 4.64 (s, 2H), 4.10 (t, J=6 Hz, 2H), 2.93-2.86 (m, 6H), 2.21-2.12 (m, 2H), 1.94-1.90 (m, 4H).

Workup

customthe solvent was evaporated
additionThe resulting residue was diluted with water
extractionextracted with dichloromethane
dry with materialThe dichloromethane extracts were dried over MgSO4
concentrationconcentrated
customto give a white solid, 0.36 g
customA small amount of the product was purified by semi-prep LC-MS

Sources & evidence

ORD record: ord-1070cd21a3be443092f1803f78cb2dac
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528262B2

Reaction notes

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