Chlorosuccinimide → 2-(9-Chloro-7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 515735Notes

Reaction equation

HRID 515735 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH:29]([CH3:31])[CH3:30])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([OH:23])=[O:22])[C:12]3=[CH:11][C:10]=2[C:9]=1[CH3:24])#[N:2].[Cl:32]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:32][C:11]1[C:10]2[C:9]([CH3:24])=[C:8]([O:7][CH2:6][C:5]3[CH:25]=[CH:26][C:27]([O:28][CH:29]([CH3:31])[CH3:30])=[C:3]([C:1]#[N:2])[CH:4]=3)[CH:16]=[CH:15][C:14]=2[N:13]2[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([OH:23])=[O:22])[C:12]=12

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 583295982-(7-(3-Cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

Product 1

HCID 583296012-(9-Chloro-7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic AcidYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid (30 mg, 0.072 mmol) in DCM (2 mL) was added N-chlorosuccinimide (10.1 mg, 0.075 mmol) at 0° C. The reaction was stirred at that temperature for 40 min, diluted with DCM, washed with aqueous Na2S2O3 solution and water, and dried over anhydrous Na2SO4. The solvent was evaporated, and the residue was passed through a silica gel column with 5% MeOH/DCM to give the title compound as beige solid (23 mg). LCMS m/z=453.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.41 (d, J=6.0 Hz, 6H), 2.29-2.38 (m, 1H), 2.58 (dd, J=16.7, 10.5 Hz, 1H), 2.66 (s, 3H), 2.88-2.98 (m, 1H), 3.33 (dd, J=16.7, 3.7 Hz, 1H), 3.76-3.84 (m, 1H), 3.90-3.98 (m, 1H), 4.05-4.13 (m, 1H), 4.62-4.68 (m, 1H), 4.94 (s, 2H), 6.84 (d, J=8.8 Hz, 1H), 6.95-6.98 (m, 2H), 7.56-7.62 (m, 2H).

Workup

  1. washwashed with aqueous Na2S2O3 solution and water
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-46ef2418b4bc4b4388c6d45ac67ee575
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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