Tributylphosphine → HCID 11677782, compound

HRID 1173417Notes

Reaction equation

HRID 1173417 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.O[C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:25][CH:24]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.C(P(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([N:4]([CH2:17][C:18]([F:19])([F:20])[F:21])[CH2:3][CH2:2][O:1][C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[CH:27][CH:28]=2)=[CH:6][C:7]=1[C:13]([F:15])([F:16])[F:14])#[N:10]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2756771N-Boc-4-hydroxyanilineHCID 866237314-[(2-Hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 11677782HCID 11677782, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[(2-hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.100 g, 0.32 mmol), 1,1-dimethylethyl (4-hydroxyphenyl)carbamate (0.0737 g, 0.35 mmol) and ADDP (0.121 g, 0.48 mmol) in THF (3.5 mL) at rt was added tri-n-butylphosphine (0.12 mL, 0.48 mmol). The resulting mixture was stirred 1 hour at rt and diluted with EtOAc until homogeneous. The resulting solution was extracted with 1 N NaOH (×2), washed (water, brine), dried over Na2SO4 and filtered. The filtrate was adsorbed onto a minimal amount of silica gel and purified by flash chromatography (EtOAc/hexanes), affording 0.133 g of the title compound as a colorless gum: 1H NMR (400 MHz, CDCl3) δ 7.66 (d, J=9.0 Hz, 1H), 7.26 (app. d, J=8.3 Hz, 2H), 7.16 (d, J=2.3 Hz, 1H), 6.98 (dd, J=9.0, 2.5 Hz, 1H), 6.80-6.75 (m, 2H), 6.38 (bs, 1H), 4.24-4.14 (m, 4H), 3.97 (t, J=5.1 Hz, 2H), 1.50 (s, 9H); MS (ESI) m/z 502 (M−1).

Workup

  1. extractionThe resulting solution was extracted with 1 N NaOH (×2)
  2. washwashed (water, brine)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. custompurified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-ff461a94b8894e39a7b10bc2e7e31a69
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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