Dimethylformamide → 6-[2-cyclopentyl-4-(3-fluoro-4-isopropylphenyl)-2-hydroxybut-3-ynyl]-2,2-dimethyl-4H-1,3-dioxin-4-one
Reaction equation
[Br:1][c:2]1[cH:3][c:4]([F:11])[c:5]([CH:8]([CH3:9])[CH3:10])[cH:6][cH:7]1.[CH3:43][CH2:44][O:45][C:46]([CH3:47])=[O:48].[CH:12]1([C:17]([CH2:18][C:19]2=[CH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:26])[O:24]2)([C:28]#[CH:29])[OH:30])[CH2:13][CH2:14][CH2:15][CH2:16]1.[CH:31]([NH:32][CH:33]([CH3:34])[CH3:35])([CH3:36])[CH3:37].[Cu:49][I:50].[O:38]=[CH:39][N:40]([CH3:41])[CH3:42].[Pd:51]([Cl:52])[Cl:53].[c:54]1([P:55]([c:56]2[cH:57][cH:58][cH:59][cH:60][cH:61]2)[c:62]2[cH:63][cH:64][cH:65][cH:66][cH:67]2)[cH:68][cH:69][cH:70][cH:71][cH:72]1.[c:73]1([P:74]([c:75]2[cH:76][cH:77][cH:78][cH:79][cH:80]2)[c:81]2[cH:82][cH:83][cH:84][cH:85][cH:86]2)[cH:87][cH:88][cH:89][cH:90][cH:91]1>>[c:2]1([C:29]#[C:28][C:17]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)([CH2:18][C:19]2=[CH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:26])[O:24]2)[OH:30])[cH:3][c:4]([F:11])[c:5]([CH:8]([CH3:9])[CH3:10])[cH:6][cH:7]1Participants
9
Reactant 8
HCID 6228Dimethylformamide
HCID 7912Diisopropylamine
HCID 8857Ethyl Acetate
HCID 11776Triphenylphosphine2×
HCID 24290Palladium Chloride
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
HCID 210510924-Bromo-2-fluoro-1-(1-methylethyl)benzene
HCID 224998026-(2-Cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-oneProduct 1
Sources & evidence
- ORD record
- ord-b54dc92908694bed8e9aa687c5426cc7
- Source dataset
- Validation data from https://doi.org/10.1039/C8SC04228D
Reaction notes
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