5-Chloro-6-iodo-1,3-dihydro-isoindole-2-carboxylic Acid Tert-Butyl Ester → 5-Chloro-6-(2,5-dihydro-furan-3-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

HRID 225662Notes

Reaction equation

HRID 225662 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12](I)=[C:13]([Cl:17])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:24]1[CH2:25][O:26][CH2:27][CH:28]=1)CCC>>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:24]3[CH2:25][O:26][CH2:27][CH:28]=3)=[C:13]([Cl:17])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 577534555-Chloro-6-iodo-1,3-dihydro-isoindole-2-carboxylic Acid Tert-Butyl EsterHCID 68822896Tributyl-(2,5-dihydro-furan-3-yl)-stannane

Product 1

HCID 577532285-Chloro-6-(2,5-dihydro-furan-3-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

Procedure

Prepared in analogy to Example A49(a) from 5-chloro-6-iodo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (Example A3(c)) and tributyl-(2,5-dihydro-furan-3-yl)-stannane. Off-white solid. MS (m/e): 268.3 ([{37Cl} M+H−Me2C═CH2]+, 32%), 266.1 ([{35Cl}M+H−Me2C═CH2]+, 100%).

Sources & evidence

ORD record
ord-725c82d9e5774fcf9135d236da4fab51
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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