Water → HCID 69893584, compound

HRID 393225Notes

Reaction equation

[NH2:1][CH:2]([CH3:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[NH:6][CH:5]=1.C([O-])(O)=O.[Na+].O.ClC([O:24][CH2:25][CH:26]1C2C=CC=CC=2C2[C:27]1=CC=CC=2)=O>O1CCOCC1>[NH2:1][CH:2]([CH3:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:25](=[O:24])[CH2:26][CH3:27])[CH:11]=2)[NH:6][CH:5]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A 35 mL round bottom flask was charged with 3-(2-aminopropyl)-1H-indol-5-ol (0.20 g, 0.65 mmol) was added NaHCO3 (0.9 g, 11 mmol), water (2 mL) and 1,4-dioxane (8 mL). 9-Fluorenylmethyl chloroformate (0.20 g, 0.82 mmol) was added and the mixture stirred for 16 h at 23° C. TLC analysis indicated that the reaction was complete and the solution decanted into aqueous NaHCO3, then extracted with ether (2×30 mL). The combined organic extracts were washed with water (20 mL), dried over MgSO4 and concentrated. The crude product was purified by chromatography (silica, 65:35 hexanes:ethyl acetate) to furnish the title compound (0.26 g, 97%): 1H NMR (CDCl3) δ 7.88 (bs, 1H), 7.76 (d, J =6 Hz, 2H), 7.57 (d, J=6 Hz, 2H), 7.44-7.19 (m, 6H), 7.07 (s, 1H), 6.94 (s, 1H), 6.77 (dd, J=8, 2 Hz, 1H), 4.8 (m. 1H), 4.45 (m, J=8 Hz, 2H), 4.20 (m, J=8 Hz, 1H), 2.81 (bm, 2H), 1.15 (d, J=8 Hz); MS(ESI) m/z 430 (M+NH4)+, 413 (M+H)+.

Workup

customthe solution decanted into aqueous NaHCO3
extractionextracted with ether (2×30 mL)
washThe combined organic extracts were washed with water (20 mL)
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude product was purified by chromatography (silica, 65:35 hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-213b3dbd98e04adfaa61c32365119c3b
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806285B1

Reaction notes

Loading…