22557-04-6 → HCID 86628473, compound

HRID 1618437Notes

Reaction equation

HRID 1618437 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:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)[CH2:20][C:21]#[CH:22]>>[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]([C:22]#[C:21][CH2:20][CH2:19][C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=2)[CH:10]=1)=[O:4]

Participants

3

Reactant 2

HCID 1340706322557-04-6HCID 86628472HCID 86628472, compound

Product 1

HCID 86628473HCID 86628473, compound

Procedure

Sonogashira reaction of (2,2,2-trifluoro-N-(3-hydroxy-3-(3-iodophenyl)propyl)acetamide) with 1-(but-3-ynyl)-4-methylbenzene yielded 2,2,2-trifluoro-N-(3-hydroxy-3-(3-(4-p-tolylbut-1-ynyl)phenyl)propyl)acetamide as yellow oil. Yield (0.310 g, 60%): 1H NMR (400 MHz, CDCl3) δ 7.29-7.51 (m, 4H), 7.17 (d, J=8.0 Hz, 2H), 7.13 (d, J=8.0 Hz, 2H), 4.84-4.86 (m, 1H), 3.66-3.70 (m, 1H), 3.38-3.43 (m, 1H), 2.89 (t, J=7.6 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H), 2.33 (s, 3H), 2.25 (bs, 1H), 1.92-1.97 (m, 2H).

Sources & evidence

ORD record
ord-4b534cff068649b391757a802d939b9b
Source dataset
uspto-grants-2014_07
Patent number
US08766007B2

Reaction notes

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