3-Iodophenol → 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

HRID 858602Notes

Reaction equation

HRID 858602 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#[N:12])[CH2:10][CH2:9]2)=[C:4]([F:13])[CH:3]=1.IC1C=C(O)C=CC=1.[CH:22]1([C:27]([OH:44])([C:38]#[C:39][Si](C)(C)C)[CH2:28][C:29]2[O:34][C:33]([CH3:36])([CH3:35])[O:32][C:31](=[O:37])[CH:30]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH:22]1([C:27]([OH:44])([CH2:28][C:29]2[O:34][C:33]([CH3:35])([CH3:36])[O:32][C:31](=[O:37])[CH:30]=2)[C:38]#[C:39][C:2]2[CH:7]=[CH:6][C:5]([C:8]3([C:11]#[N:12])[CH2:10][CH2:9]3)=[C:4]([F:13])[CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 122723-IodophenolHCID 224997936-(2-Cyclopentyl-2-hydroxy-4-trimethylsilanyl-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-oneHCID 587623291-(4-Bromo-2-fluorophenyl)cyclopropane-1-carbonitrile

Product 1

HCID 587623341-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile

Procedure

The desired product was prepared analogously to example F(7), Step 5, substituting 1-(4-bromo-2-fluoro-phenyl)-cyclopropanecarbonitrile (0.96 g, 4.0 mmol), from Step 2 above in place of 3-iodophenol, and 6-(2-cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one (1.06 g, 4.0 mmol; from Step 4 above) in place of 6-but-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione. Yield: 1.241 g, 73%.

Sources & evidence

ORD record
ord-d106cbfb8d6c4ed990f80cc20efe3c3e
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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