Hydrogen iodide → HCID 51347406, compound

HRID 2063712Notes

Reaction equation

[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[CH2:19][C:20]([O:22]CC)=[O:21])=[CH:10][CH:9]=2)=[O:7])=[C:4]([CH3:27])[CH:3]=1.I>>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[CH2:19][C:20]([OH:22])=[O:21])=[CH:12][CH:13]=2)=[O:7])=[C:4]([CH3:27])[CH:3]=1

Participants

Reactant 2

HCID 24841Hydrogen iodide

HCID 67086014HCID 67086014, compound

Product 1

HCID 51347406HCID 51347406, compoundYield 36%

Procedure

Example 89 (pale yellow oil, 0.017 g, 0.047 mmol, 36% yield) was prepared from ethyl 2-(1-(4-(4-chloro-2-methylbenzoyl)phenyl)pyrrolidin-2-yl)acetate (88E) following the procedure of 86H. LC-MS Anal. Calc'd for C20H20ClNO3 357. found [M+H] 358. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.4 (1H, brs), 7.55 (2H, d, J=8.8 Hz), 7.43 (1H, d, J=1.2 Hz), 7.36 (1H, dd, J=1.2, 8.0 Hz), 7.24 (1H, d, J=8.0 Hz), 6.62 (2H, d, J=8.8 Hz), 4.17 (1H, m), 3.47 (1H, m), 3.22 (1H, m), 2.58 (1H, m), 2.30 (1H, m), 2.17 (3H, s), 2.06 (3H, m), 1.99 (1H, m). Analytical HPLC: RT=18.7 min, HI: 92.9%.

Sources & evidence

ORD record: ord-0c0750ed19344950a7dc9dd6e4321568
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288404B2

Reaction notes

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