2-Iodo-1,3-oxazole → 4-[(2-{[4-(1,3-Oxazol-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

HRID 1173431Notes

Reaction equation

HRID 1173431 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]([CH2:31][C:32]([F:35])([F:34])[F:33])[C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=3)=[CH:11][CH:10]=2)O1.I[C:38]1[O:39][CH:40]=[CH:41][N:42]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:39]1[CH:40]=[CH:41][N:42]=[C:38]1[C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][N:18]([CH2:31][C:32]([F:33])([F:34])[F:35])[C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:28])([F:29])[F:30])[CH:20]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 183592092-Iodo-1,3-oxazole2×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

Product 1

HCID 116981894-[(2-{[4-(1,3-Oxazol-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Synthesized as described in Example 40B from 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 (Example 40A) and 2-iodo-1,3-oxazole (step A above), with the following exceptions: additional 2-iodo-1,3-oxazole (0.3 equiv) was added after 2 h of heating, additional Pd(PPh3)4 (0.005 g) was added after 4 h of heating, and heating was maintained for only 6 h: MS (ESI) m/z 456 (M+1).

Workup

  1. customSynthesized
  2. temperatureof heating
  3. temperatureof heating
  4. temperatureheating
  5. temperaturewas maintained for only 6 h

Sources & evidence

ORD record
ord-9d9d6438dec44a2aab98dbe0918cc714
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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