Triphenylphosphine → HCID 86623737, compound

HRID 1173449Notes

Reaction equation

HRID 1173449 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][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:31][C:32]2[N:37]=[CH:36][C:35](O)=[CH:34][CH:33]=2)=[CH:26][CH:25]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:31][C:32]2[N:37]=[CH:36][C:35]([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:34][CH:33]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 11776TriphenylphosphineHCID 59557193HCID 59557193, compoundHCID 866237314-[(2-Hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 86623737HCID 86623737, compound

Procedure

Synthesized as described in Example 27B from 4-[(2-hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (Example 15B) and 6-({[4-(methyloxy)phenyl]methyl}oxy)-3-pyridinol (step B above) with the following exceptions: PPh3 was used instead of PBu3, and the reaction was started at 0° C., then allowed to proceed at rt: 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J=3.3 Hz, 1H), 7.68 (d, J=8.9 Hz, 1H), 7.37 (m, 2H; AA′XX′), 7.18 (d, J=2.7 Hz, 1H), 7.15 (dd, J=8.9, 3.1 Hz, 1H), 7.00 (dd, J=8.9, 2.7 Hz, 1H), 6.90 (m, 2H; AA′XX′), 6.72 (d, J=8.9 Hz, 1H), 5.23 (s, 2H), 4.20 (t, J=5.1 Hz, 2H; overlapping 4.19), 4.19 (q, J=8.6 Hz, 2H; overlapping 4.20), 3.99 (t, J=5.2 Hz, 2H), 3.81 (s, 3H).

Workup

  1. customSynthesized
  2. customwas started at 0° C.
  3. customto proceed at rt

Sources & evidence

ORD record
ord-dbdcd586b4be440ebc04c60086c1ce37
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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