Trifluoroacetic acid → HCID 59187019, compound

HRID 456039Notes

Reaction equation

HRID 456039 reaction equation
C([NH:5][C:6]1[C:11]([Cl:12])=[C:10]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[C:17]=2[O:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[O:15])[C:9]([Cl:36])=[CH:8][N:7]=1)(C)(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>ClC(Cl)C>[NH2:5][C:6]1[C:11]([Cl:12])=[C:10]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[C:17]=2[O:26][CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)=[O:15])[C:9]([Cl:36])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59187018HCID 59187018, compound

Product 1

HCID 59187019HCID 59187019, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-(2-tert-Butylamino-3,5-dichloro-pyridin-4-yl)-1-{2-[2-(4-fluoro-phenyl)-ethoxy]-3,4-dimethoxy-phenyl}-ethanone obtained from example 300 (16.5 mg, 0.0308 mmol), triethylsilane (2 eq.) and TFA (0.1 mL) in dichloroethane (0.2 mL) was heated to 50° C. for 24 hours. The crude mixture was evaporated in vacuo, redissolved in dichloroethane (1 mL) and washed with NaHCO3 (sat, 2×0.5 mL). The organic phase was dried over Na2SO4 and the solvent evaporated in vacuo. Pure 2-(2-amino-3,5-dichloro-pyridin-4-yl)-1-{2-[2-(4-fluoro-phenyl)-ethoxy]-3,4-dimethoxy-phenyl}-ethanone was obtained by flash chromatography using a gradient of MeOH in dichloromethane as eluent.

Workup

  1. customThe crude mixture was evaporated in vacuo
  2. dissolutionredissolved in dichloroethane (1 mL)
  3. washwashed with NaHCO3 (sat, 2×0.5 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-724c07b99650409a93c249ea50c256f8
Source dataset
uspto-grants-2013_07
Patent number
US08497380B2

Reaction notes

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