4-Cyanophenylboronic acid → HCID 51034671, compound

HRID 1623489Notes

Reaction equation

HRID 1623489 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[CH3:12][O:13][C:14](=[O:38])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]([C:30](=[O:37])[C:31]#[C:32][C:33]([OH:36])([CH3:35])[CH3:34])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2I)[CH:16]=1>>[CH3:12][O:13][C:14](=[O:38])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)/[C:31](=[C:32](\[C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)/[C:33]([OH:36])([CH3:35])[CH3:34])/[C:30]2=[O:37])[CH:16]=1

Participants

3

Reactant 2

HCID 27343264-Cyanophenylboronic acidHCID 67036364HCID 67036364, compound

Product 1

HCID 51034671HCID 51034671, compound

Procedure

The title compound was prepared in analogy to Example 84 starting from 4-cyano-phenylboronic acid (commercially available) and 3-{[(4-hydroxy-4-methyl-pent-2-ynoyl)-(2-iodo-phenyl)-amino]-methyl}-benzoic acid methyl ester. 1H NMR (400 MHz, DMSO-d6) δppm 1.33 (s, 6H) 3.85 (s, 3H) 5.15 (s, 2H) 5.35 (d, J=7.83 Hz, 1H) 6.68 (t, J=7.71 Hz, 1H) 7.03 (d, J=7.83 Hz, 1H) 7.15 (t, J=7.71 Hz, 1H) 7.48-7.55 (m, 1H) 7.52 (d, J=7.58 Hz, 3H) 7.62 (d, J=7.83 Hz, 1H) 7.89 (d, J=7.83 Hz, 1H) 7.99 (s, 1H) 8.05 (d, J=8.34 Hz, 2H).

Sources & evidence

ORD record
ord-6ea1b849bbc94241a873cf1ebe3cb699
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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