4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 4-[(2-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

HRID 1173429Notes

Reaction equation

HRID 1173429 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.[CH3:22][C:23]1([CH3:37])[C:27]([CH3:29])([CH3:28])[O:26][B:25]([C:30]2[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=2)[O:24]1>COCCOC>[CH3:28][C:27]1([CH3:29])[C:23]([CH3:22])([CH3:37])[O:24][B:25]([C:30]2[CH:35]=[CH:34][C:33]([O:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:19])([F:20])[F:21])[C:5]3[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:15])([F:16])[F:14])[CH:6]=3)=[CH:32][CH:31]=2)[O:26]1

Participants

4

Reactant 2

HCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 866237314-[(2-Hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 866237354-[(2-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Synthesized as described in Example 27B from 4-[(2-hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (Example 15B) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, using dry DME as the reaction solvent: 1H NMR (400 MHz, CDCl3) δ 7.74 (m, 2H; AA′XX′), 7.67 (d, J=8.9 Hz, 1H), 7.16 (d, J=2.7 Hz, 1H), 6.99 (dd, J=8.9, 2.7 Hz, 1H), 6.84 (m, 2H; AA′XX′), 4.24 (t, J=5.2 Hz, 2H; partially overlapping 4.20), 4.20 (q, J=8.5 Hz, 2H; partially overlapping 4.24), 4.00 (t, J=5.1 Hz, 2H), 1.33 (s, 12H).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-f6b02dbf5aa24c72ab02a3004c9bbdb3
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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