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

HRID 1964137Notes

Reaction equation

HRID 1964137 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH:28]([CH3:30])[CH3:29])[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[CH:9]=1)#[N:2].C1C(=O)N([Cl:38])C(=O)C1>C(Cl)Cl>[Cl:38][C:11]1[C:10]2[CH:9]=[C:8]([O:7][CH2:6][C:5]3[CH:24]=[CH:25][C:26]([O:27][CH:28]([CH3:30])[CH3:29])=[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 672491622-(7-(3-Cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

Product 1

HCID 583295802-(9-Chloro-7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic AcidYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(7-(3-Cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid (50 mg, 0.124 mmol) was dissolved in DCM (1 mL) and cooled to 0° C. NCS (16.51 mg, 0.124 mmol) was added and the reaction was stirred at 0° C. for 15 min in a 20 mL sealed scintillation vial. The mixture was diluted with DCM and washed with water (2×10 mL), Na2S2O3 (aq) (2×10 mL), dried over MgSO4, and filtered by vacuum filtration through a glass fiber paper. The solvent was removed under reduced pressure to give the title compound (50.1 mg) as a yellow solid. LCMS m/z=439.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δppm 1.32 (d, J=6.06 Hz, 6H), 2.24-2.35 (m, 1H), 2.52-2.59 (m, 1H), 2.77-2.87 (m, 1H), 2.94 (dd, J=16.29, 4.04 Hz, 1H), 3.64-3.73 (m 1H), 3.96-4.07 (m, 1H), 4.10-4.20 (m, 1H), 4.79 (dt, J=12.09, 6.02 Hz, 1H), 5.07 (s, 2H), 6.86 (dd, J=8.72, 2.40 Hz, 1H), 6.96 (d, J=2.27 Hz, 1H), 7.29 (dd, J=8.84, 3.79 Hz, 2H), 7.72 (dd, J=8.78, 2.21 Hz, 1H), 7.79 (d, J=2.15 Hz, 1H), 12.35 (s, 1H).

Workup

  1. customsealed scintillation vial
  2. washwashed with water (2×10 mL), Na2S2O3 (aq) (2×10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered by vacuum filtration through a glass fiber paper
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c2324441619a4044a184860e057d4ba8
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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