HCID 86628472, compound → HCID 87082384, compound

HRID 341629Notes

Reaction equation

HRID 341629 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][CH2:6][CH2:7][CH:8]([OH:16])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11](I)[CH:10]=1)=[O:4].[CH2:19]([C:23]1[CH:36]=[CH:35][CH:34]=[CH:33][C:24]=1[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH2:20][C:21]#[CH:22]>>[Si:26]([O:25][C:24]1[CH:33]=[CH:34][CH:35]=[CH:36][C:23]=1[CH2:19][CH2:20][C:21]#[C:22][C:11]1[CH:10]=[C:9]([CH:8]([OH:16])[CH2:7][CH2:6][NH:5][C:3](=[O:4])[C:2]([F:18])([F:17])[F:1])[CH:14]=[CH:13][CH:12]=1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 86628472HCID 86628472, compoundHCID 87082538HCID 87082538, compound

Product 1

HCID 87082384HCID 87082384, compound

Procedure

Sonogashira reaction of the iodide (2,2,2-trifluoro-N-(3-hydroxy-3-(3-iodophenyl)propyl)acetamide) with (2-(but-3-ynyl)phenoxy)(tert-butyl)dimethylsilane yielded N-(3-(3-(4-(2-(tert-butyldimethylsilyloxy)phenyl)but-1-ynyl)phenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide as brown oil. Yield (0.220 g, 41%): 1H NMR (400 MHz, DMSO-d6) δ 9.36 (bs, 1H), 7.26-7.31 (m, 4H), 7.19-7.21 (m, 1H), 7.11 (t, J=6.0 Hz, 1H), 6.96 (t, J=6.0 Hz, 1H), 6.88 (d, J=8.0 Hz, 1H), 5.39 (d, J=4.4 Hz, 1H), 4.53-4.56 (m, 1H), 3.22-3.24 (m, 2H), 2.85 (t, J=7.6 Hz, 2H), 2.65 (t, J=7.6 Hz, 2H), 1.75-1.81 (m, 2H), 1.0 (s, 9H), 0.23 (s, 6H).

Sources & evidence

ORD record
ord-82f782072e0b4b6183fab7c55a110a55
Source dataset
uspto-grants-2014_11
Patent number
US08895782B2

Reaction notes

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