1-(4-Bromo-2-fluorophenyl)cyclopropane-1-carbonitrile → 1-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile

HRID 1453082Notes

Reaction equation

HRID 1453082 reaction equation
[CH:1]1([C:6]([OH:31])([CH2:21][C:22]2[O:23]C(C)(C)[O:25][C:26](=O)[CH:27]=2)[C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:18]#[N:19])[CH2:17][CH2:16]3)=[C:11]([F:20])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.BrC1C=CC(C2(C#N)CC2)=C(F)C=1.C1(C2(CCC3C=CC(C(C)(C)C#N)=C(F)C=3)CC(=O)CC(=O)O2)CCCC1>>[CH:1]1([C:6]2([CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][C:12]([C:15]4([C:18]#[N:19])[CH2:16][CH2:17]4)=[C:11]([F:20])[CH:10]=3)[CH2:21][C:22](=[O:23])[CH2:27][C:26](=[O:25])[O:31]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 587623291-(4-Bromo-2-fluorophenyl)cyclopropane-1-carbonitrileHCID 587623341-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopropanecarbonitrileHCID 587624232-{4-[2-(2-cyclopentyl-4,6-dioxotetrahydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl)-2-methylpropanenitrile

Product 1

HCID 587627061-{4-[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile

Procedure

The desired product was prepared analogously to step 4 of Example A(97), substituting 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile [prepared analogously to step 3 of Example A(97) substituting 1-(4-bromo-2-fluoro-phenyl)-cyclopropanecarbonitrile in place of 2-(4-bromo-2-fluorophenyl)-2-methylpropanenitrile)] in place of 2-{4-[2-(2-cyclopentyl-4,6-dioxotetrahydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl}-2-methylpropanenitrile. 1H NMR (CDCl3) δ: 1.27-1.30 (m, 2H), 1.51-1.73 (m, 10H), 1.84-1.89 (m, 2H), 2.19 (p, J=8.08 Hz, 1H), 2.58-2.71 (m, 4H), 3.36 (d, J=4.04 Hz, 2H), 6.81-6.86 (m, 2H), 7.16-7.18 (m, 1H). MS (ESI): 368 (M−H).

Sources & evidence

ORD record
ord-0569d61cff284bfd92d6e302a7576316
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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