4-Methoxybut-1-yne → Tert-butyl 3-(3-(4-methoxybut-1-ynyl)phenyl)propylcarbamate

HRID 2098517Notes

Reaction equation

HRID 2098517 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1.[CH3:19][O:20][CH2:21][CH2:22][C:23]#[CH:24]>>[CH3:19][O:20][CH2:21][CH2:22][C:23]#[C:24][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 5421524-Methoxybut-1-yneHCID 57219374Tert-butyl 3-(3-bromophenyl)propylcarbamate

Product 1

HCID 66743328Tert-butyl 3-(3-(4-methoxybut-1-ynyl)phenyl)propylcarbamate

Procedure

Sonogashira reaction of bromide 57 with 4-methoxybut-1-yne gave tert-butyl 3-(3-(4-methoxybut-1-ynyl)phenyl)propylcarbamate as yellow oil. Yield (0.83 g, 77%): 1H NMR (400 MHz, CDCl3) δ 7.22-7.25 (m, 2H), 7.16-7.21 (m, 1H), 7.09 (d, J=7.6 Hz, 1H), 4.51 (bs, 1H), 3.60 (t, J=7.8 Hz, 2H), 3.41 (s, 3H), 3.10-3.16 (m, 2H), 2.69 (t, J=7.0 Hz, 2H), 2.59 (t, J=7.6 Hz, 2H), 1.76-1.84 (m, 2H), 1.44 (s, 9H).

Sources & evidence

ORD record
ord-19cd1e9d91c448f2a0b17033edbe887a
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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