5-Iodo-1H-indole → tert-Butyl 5-cyano-1,3-dihydro-2H-isoindole-2-carboxylate

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]2.IC1C=C2C(=CC=1)[NH:24][CH:23]=C2>>[C:23]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:5]2)#[N:24]

Participants

Reactant 2

HCID 27823135-Iodo-1H-indole

HCID 57753580tert-Butyl 5-iodoisoindoline-2-carboxylate

Product 1

HCID 18630967tert-Butyl 5-cyano-1,3-dihydro-2H-isoindole-2-carboxylate

Procedure

When the product of Step B was substituted for 5-iodoindole in Example 7, Step A, the similar process afforded the title compound in 85%, as colourless solid, after purification by FCC (SiO2; CH2Cl2). 1H-NMR (CDCl3) 1.49 (s, 9H); 4.56-4.72 (m, 4H); 7.32-7.37 (m, 1H); 7.49-7.56 (m, 2H).

Sources & evidence

ORD record: ord-4707dcd7acab470a8b62e34432dfe7c1
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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