Acetic acid ethanol → HCID 178481826, compound

HRID 570236Notes

Reaction equation

HRID 570236 reaction equation
[C:1]([Si:5]([CH3:44])([CH3:43])[O:6][CH2:7][CH2:8][O:9][C:10]1[C:15]([N+:16]([O-])=O)=[C:14]([NH:19][C:20]([C:22]2[N:23]([CH3:32])[N:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=2[Cl:27])=O)[CH:13]=[C:12]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[C:39]([F:42])([F:41])[F:40])[N:11]=1)([CH3:4])([CH3:3])[CH3:2].CC(O)=O.CCO>[Fe].CCOC(C)=O>[C:28]([C:25]1[C:26]([Cl:27])=[C:22]([C:20]2[NH:16][C:15]3[C:10]([O:9][CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:44])[CH3:43])=[N:11][C:12]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]([F:40])([F:42])[F:41])=[CH:13][C:14]=3[N:19]=2)[N:23]([CH3:32])[N:24]=1)([CH3:29])([CH3:30])[CH3:31]

Participants

5

Reactant 2

HCID 18476134Acetic acid ethanolHCID 674132015-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-yl]-amide

Product 1

HCID 178481826HCID 178481826, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-yl]-amide (428 mg, 0.650 mmol, prepared as described in the previous step) and iron powder (291 mg, 5.22 mmol) in 1:1 AcOH/EtOH (7 mL) was stirred at 100° C. under Ar for 1 h. After cooling to room temperature, the mixture was treated with EtOAc (20 mL) and filtered through diatomaceous earth. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (0:100-10:90 EtOAc/hexanes) to yield 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine as a white solid. 1H-NMR (400 MHz, CD3OD) δ: 7.81 (d, 1H), 7.65-7.71 (m, 1H), 7.55-7.62 (m, 2H), 7.31 (s, 1H), 4.64 (t, J=4.9 Hz, 2H), 4.02-4.10 (m, 5H), 1.44 (s, 9H), 0.86 (s, 9H), 0.06 (s, 6H). Mass Spectrum (LCMS, ESI pos.) Calculated For C29H37ClF3N5O2Si: 608.2 (M+H), Measured: 608.3.

Workup

  1. customprepared
  2. temperatureAfter cooling to room temperature
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by flash chromatography on silica gel (0:100-10:90 EtOAc/hexanes)

Sources & evidence

ORD record
ord-95dd586ac6c4459f8716fd34433b7683
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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