Diisopropylethylamine → 5-Iodo-2-tritylisoindoline

HRID 710282

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:4]=1[CH2:10]Br.[C:12]([NH2:31])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[I:9][C:6]1[CH:5]=[C:4]2[C:3](=[CH:8][CH:7]=1)[CH2:2][N:31]([C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:10]2

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the product of Step B (0.34 g; 0.87 mmol) hydrochloride salt of tritylamine (0.22 g; 0.87 mmol) and N,N-diisopropylethylamine (DIPEA) (0.49 ml; 2.8 mmol) in anhydrous DMF (3 ml) was stirred for 2 h at 60° C. under N2. After removing the solvent in vacuo, the residue was diluted to 15 ml with ethyl acetate (EtOAc) and washed with, H2O, brine and dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (SiO2; hexane/EtOAc, 8:2) to give pure title compound (0.2 g; 48%) as colourless heavy syrup. 1H-NMR (CDCl3) 3.86 (s, 2H); 3.87 (s, 2H); 6.81-7.57 (m, 18H).

Workup

customAfter removing the solvent in vacuo
additionthe residue was diluted to 15 ml with ethyl acetate (EtOAc)
washwashed with, H2O, brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customThe filtrate was evaporated to dryness under reduced pressure
customthe residue was purified by FCC (SiO2; hexane/EtOAc, 8:2)

Sources & evidence

ORD record: ord-2b25a432ae864e688dac041a97b72a02
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Linked notes

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