Tributylphosphine → HCID 11718168, compound

HRID 1173468Notes

Reaction equation

HRID 1173468 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:4]([CH2:17][CH2:18][OH: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.[F:22][C:23]1[N:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.P(CCCC)(CCCC)CCCC>>[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:4]([CH2:17][CH2:18][O:19][C:26]1[CH:27]=[N:28][C:23]([F:22])=[CH:24][CH:25]=1)[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:14])([F:15])[F:16])[CH:6]=1

Participants

5

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 27631086-Fluoropyridin-3-olHCID 68495138HCID 68495138, compound

Product 1

HCID 11718168HCID 11718168, compound

Procedure

Synthesized as described in Example 27B from 4-[(2,2-dimethylpropyl)(2-hydroxyethyl)amino]-2-(trifluoromethyl)benzonitrile (Example 61C) and 6-fluoro-3-pyridinol (Example 51A) with the following exceptions: additional portions of ADDP and PBu3 (0.5 equiv ea) were added to the reaction mixture after 1 h, the reaction was stirred for 60 h, and the title compound was purified by flash chromatography (EtOAc/hexanes) followed by RP-HPLC (MeCN/H2O+0.1% TFA): MS (ESI) m/z 396 (M+1).

Workup

  1. customSynthesized
  2. customthe title compound was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-98683aa245c3460ea85b2dbfac4be5e5
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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