Diisobutylamine → 5-(2-Diisobutylamino-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966529Notes

Reaction equation

[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21]OS(C)(=O)=O)[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([NH:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:29]([CH3:31])[CH3:30]>O1CCOCC1>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N:32]([CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:28][CH:29]([CH3:31])[CH3:30])[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (360 mg, 0.93 mmol, Example 56, Step D) in dioxane (10 mL) was added diisobutylamine (1.62 mL, 9.3 mmol). The mixture was stirred at 100° C. overnight and then partitioned between methylene chloride and water. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a solid residue, which was purified by chromatography (20% ethyl acetate in hexanes) to give 303 mg (77%) of the desired product as a white solid: mp 134-135° C.; MS(APCI+): m/z 421.3 (MH+); Anal. Calcd for C27H36N2O2: C, 77.10; H, 8.63; N, 6.66. Found: C, 76.94; H, 8.75; N, 6.55.

Workup

custompartitioned between methylene chloride and water
washThe organic phase was washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customto give a solid residue, which
customwas purified by chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-d2c47aef91744d27b9933cd9d7213eb3
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951848B2

Reaction notes

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