1-Chloro-3-iodobenzene → HCID 86711844, compound

HRID 623762Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[CH:11][N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16](OC)[CH:15]=3)[C:9]=2[C:22]([N:24]2[CH2:27][C:26]([F:29])([F:28])[CH2:25]2)=[O:23])=[CH:4][CH:3]=1.[Cl:30]C1C=CC=C(I)C=1.ClC1C=CC(C2C(C)=CNC=2C(N2CC(F)(F)C2)=O)=CC=1>>[Cl:30][C:16]1[CH:15]=[C:14]([N:10]2[CH:11]=[C:12]([CH3:13])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[C:9]2[C:22]([N:24]2[CH2:27][C:26]([F:29])([F:28])[CH2:25]2)=[O:23])[CH:19]=[CH:18][CH:17]=1

Participants

Reactant 3

HCID 122691-Chloro-3-iodobenzene

HCID 86711845HCID 86711845, compound

HCID 86711846HCID 86711846, compound

Product 1

HCID 86711844HCID 86711844, compoundYield 89%

Procedure

[1-(3-chlorophenyl)-3-(4-chlorophenyl)-4-methyl-pyrrol-2-yl]-(3,3-difluoroazetidin-1-yl)methanone was synthesised according to the procedure described for [3-(4-Chlorophenyl)-1-(3-methoxyphenyl)-4-methyl-pyrrol-2-yl]-(3,3-difluoroazetidin-1-yl)methanone (SC-32) using 1-chloro-3-iodobenzene (1 mL, 8 mmol) and [3-(4-chlorophenyl)-4-methyl-1H-pyrrol-2-yl]-(3,3-difluoroazetidin-1-yl)methanone (200 mg, 0.6 mmol). The product was purified by preparative HPLC (preparative Agilent 1200 Series HPLC system using 30%-95% acetonitrile/water (0.1% Ammonia aq.) over 15 minutes, collecting at 254 nm) to afford the title compound as an off-white solid (223 mg, 89% yield).

Workup

custom[1-(3-chlorophenyl)-3-(4-chlorophenyl)-4-methyl-pyrrol-2-yl]-(3,3-difluoroazetidin-1-yl)methanone was synthesised
customThe product was purified by preparative HPLC (preparative Agilent 1200 Series HPLC system using 30%-95% acetonitrile/water (0.1% Ammonia aq.) over 15 minutes, collecting at 254 nm)

Sources & evidence

ORD record: ord-469d33869aa94ded8768a02cc63873fe
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302988B2

Reaction notes

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