N-Iodosuccinimide → HCID 67534215, compound

HRID 494877Notes

Reaction equation

HRID 494877 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)=[CH:14][C:12]=2[CH:13]=1.[I:26]N1C(=O)CCC1=O>>[I:26][C:13]1[C:12]2[CH:14]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=3)[CH:16]=[CH:17][C:11]=2[O:10][C:9]=1[CH2:8][CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C@H:2]1[CH3:1]

Participants

3

Reactant 2

HCID 120273N-Iodosuccinimide2×HCID 9818903Benzonitrile, 4-(2-(2-((2r)-2-methyl-1-pyrrolidinyl)ethyl)-5-benzofuranyl)-

Product 1

HCID 67534215HCID 67534215, compoundYield 18%

Procedure

The mono-(L)-tartaric acid salt of the product of Example 1D and N-iodosuccinimide were processed as in Example 156, except that a large excess of N-iodosuccinimide (2.4 molar equivalents) was utilized, to provide the title compound as a tan gum (18% yield). MS (ESI) m/z 457 (M+H)+; 1HNMR (300 MHz, CD3OD) δ 1.49 (d, 3H), 1.67-1.84 (m, 1H), 2.00-2.25 (m, 2H), 2.29-2.44 (m, 1H), 3.22-3.63 (m, 5H), 3.72-3.91 (m, 2H), 7.59-7.64 (m, 2H), 7.72 (dd, 1H), 7.80-7.89 (m, 4H).

Sources & evidence

ORD record
ord-8f192f6373b94a659d1766db6b7cc05c
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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