4-Fluorobenzonitrile → HCID 66818505, compound

HRID 1024776Notes

Reaction equation

[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[C:20]([C:22]([N:24]3[CH:33]4[CH:28]([CH2:29][CH2:30][CH2:31][CH2:32]4)[CH2:27][CH2:26][CH2:25]3)=[O:23])[CH:19]=[C:18]([OH:34])[CH:17]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].F[C:37]1[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=1>>[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:21]=[C:20]([C:22]([N:24]3[CH:33]4[CH:28]([CH2:29][CH2:30][CH2:31][CH2:32]4)[CH2:27][CH2:26][CH2:25]3)=[O:23])[CH:19]=[C:18]([O:34][C:37]3[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=3)[CH:17]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 145174-Fluorobenzonitrile

HCID 66818476HCID 66818476, compound

Product 1

HCID 66818505HCID 66818505, compoundYield 98.6%

Procedure

Using 1.34 g (2.79 mmol) of {4-[3-hydroxy-5-(octahydroquinoline-1-carbonyl)phenoxy]benzyl}carbamic acid tert-butyl ester and 4-fluorobenzonitrile (0.84 g, 6.97 mmol) and following the procedure of Example 42(b) afforded 1.6 g of the required product. 1H NMR (DMSO-d6): δ 1.30 (8H, m), 1.40 (9H, s), 1.8 (8H, m), 4.1 (2H, d), 6.68 (1H, s), 6.82 (2H, s), 7.08 (2H, d), 7.22 (2H, d), 7.28 (2H, d), 7.4 (1H, t), 7.88 (2H, d).

Sources & evidence

ORD record: ord-e5c82de61fa54f5fbce0a1901b6c59a2
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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