4-Fluorobenzonitrile → HCID 66818675, compound

HRID 1024781Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:30])[C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([O:12][C:13]2[C:18]([F:19])=[CH:17][C:16]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:15][C:14]=2[F:29])[CH:6]=1)[CH3:2].F[C:32]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=1>>[CH2:1]([O:3][C:4](=[O:30])[C:5]1[CH:10]=[C:9]([O:11][C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=2)[CH:8]=[C:7]([O:12][C:13]2[C:18]([F:19])=[CH:17][C:16]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])=[CH:15][C:14]=2[F:29])[CH:6]=1)[CH3:2]

Participants

Reactant 2

HCID 145174-Fluorobenzonitrile

HCID 66818654HCID 66818654, compound

Product 1

HCID 66818675HCID 66818675, compoundYield 48.5%

Procedure

Using 0.5 g (1.18 mmol) of 3-[4-(tert-butoxycarbonylamino-methyl)-2,6-difluoro-phenoxy]-5-hydroxy-benzoic acid ethyl ester and 4-fluorobenzonitrile (0.21 g, 1.77 mmol) and following the procedure of Example 42(b) afforded 0.3 g of the required product. 1H NMR (DMSO-d6): δ 1.25 (3H, t), 1.42 (9H, s), 4.2 (2H, d), 4.28 (2H, q), 7.22 (6H, m), 7.32 (1H, s), 7.54 (1H, t), 7.90 (2H, d).

Sources & evidence

ORD record: ord-188e28a62d69402fac1c7554e314ba6f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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