N-Iodosuccinimide → 2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 515678Notes

Reaction equation

HRID 515678 reaction equation
[CH:1]1([C:6]2[CH:29]=[CH:28][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[N:17]5[CH2:21][CH2:22][CH:23]([CH2:24][C:25]([OH:27])=[O:26])[C:16]5=[CH:15][C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:30]([F:33])([F:32])[F:31])[CH2:5][CH2:4][CH2:3][CH2:2]1.[I:34]N1C(=O)CCC1=O>>[CH:1]1([C:6]2[CH:29]=[CH:28][C:9]([CH2:10][O:11][C:12]3[CH:20]=[CH:19][C:18]4[N:17]5[CH2:21][CH2:22][CH:23]([CH2:24][C:25]([OH:27])=[O:26])[C:16]5=[C:15]([I:34])[C:14]=4[CH:13]=3)=[CH:8][C:7]=2[C:30]([F:33])([F:31])[F:32])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 120273N-IodosuccinimideHCID 461749052-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

Product 1

HCID 583295772-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

Procedure

From 2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid and 1-iodopyrrolidine-2,5-dione, in a similar manner to the one described in Example 1.4, the title compound was obtained as a brown solid. LCMS m/z=584.5 [M+H]+; 1H NMR (400 MHz, DMSO-d6) 5 ppm 1.55-1.73 (m, 4H), 1.78-1.89 (m, 2H), 1.94-2.06 (m, 2H), 2.25-2.37 (m, 1H), 2.45-2.58 (m, 1H), 2.77-2.90 (m, 1H), 3.00 (dd, J=16.36, 3.35 Hz, 1H), 3.20-3.29 (m, 1H), 3.52-3.61 (m, 1H), 4.00-4.10 (m, 1H), 4.13-4.23 (m, 1H), 5.18 (s, 2H), 6.80 (d, J=2.40 Hz, 1H), 6.87 (dd, J=8.78, 2.34 Hz, 1H), 7.26 (d, J=8.72 Hz, 1H), 7.63 (d, J=8.08 Hz, 1H), 7.70-7.78 (m, 2H), 12.30 (bs, 1H).

Sources & evidence

ORD record
ord-cd6507a662394ebcad04812c4d58f513
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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