N-Iodosuccinimide → tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

HRID 515721Notes

Reaction equation

HRID 515721 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH:32]([CH3:34])[CH3:33])[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]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:12]3=[CH:11][C:10]=2[CH:9]=1)#[N:2].C1C(=O)N([I:42])C(=O)C1>C(Cl)Cl.CC(OC)(C)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[O:31][CH:32]([CH3:34])[CH3:33])[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]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C:12]3=[C:11]([I:42])[C:10]=2[CH:9]=1)#[N:2]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 67252091tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Product 1

HCID 86654873tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-9-iodo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetateYield 98.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (0.576 g, 1.251 mmol) was dissolved in DCM (12.51 mL). The reaction mixture was cooled to 0° C., and NIS (0.295 g, 1.313 mmol) was added while stirring. After stirring at 0° C. for 50 min, the reaction mixture was diluted with MTBE (60 mL), washed with water (2×20 mL), 2 M sodium thiosulfate (2×12.5 mL), brine (10 mL), and dried over MgSO4. The solvent was evaporated in vacuo to give the title compound as a light-yellow solid (0.723 g) without further purification. LCMS m/z=587.4 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.36 (d, J=6.06 Hz, 6H), 1.40 (s, 9H), 2.34-2.45 (m, 1H), 2.52 (dd, J=15.92, 9.85 Hz, 1H), 2.87 (dt, J=18.60, 8.45 Hz, 1H), 2.99 (dd, J=15.92, 3.54 Hz, 1H), 3.57-3.65 (m, 1H), 4.05 (m, 1H), 4.17 (m, 1H), 4.75 (dt, J=12.13, 6.06 Hz, 1H), 5.06 (s, 2H), 6.83-6.85 (m, 1H), 6.85-6.89 (m, 1H), 7.14 (d, J=8.72 Hz, 1H), 7.19 (d, J=8.72 Hz, 1H), 7.67 (dd, J=8.72, 2.15 Hz, 1H), 7.70 (d, J=2.15 Hz, 1H).

Workup

  1. stirringAfter stirring at 0° C. for 50 min
  2. washwashed with water (2×20 mL), 2 M sodium thiosulfate (2×12.5 mL), brine (10 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-320bf5a822a14270a18a5e49f3236240
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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