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Trimethylsilyl iodide → 1-(3-tert-Butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-((5-fluoro-2-(1-(2-oxoethyl)-1H-indazol-5-yloxy)phenyl)methyl)urea

HRID 1666758
Notes
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Reaction equation

HRID 1666758 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[N:28]([CH2:32][CH:33](OC)[O:34]C)[N:27]=[CH:26]3)=[O:12])[N:7]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].I[Si](C)(C)C>ClCCl>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[N:28]([CH2:32][CH:33]=[O:34])[N:27]=[CH:26]3)=[O:12])[N:7]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 575522961-(3-tert-Butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-((2-(1-(2,2-dimethoxyethyl)-1H-indazol-5-yloxy)-5-fluorophenyl)methyl)urea

Product 1

HCID 575522811-(3-tert-Butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-((5-fluoro-2-(1-(2-oxoethyl)-1H-indazol-5-yloxy)phenyl)methyl)ureaYield 116.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent
2×

Procedure

1-(3-tert-Butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-((2-(1-(2,2-dimethoxyethyl)-1H-indazol-5-yloxy)-5-fluorophenyl)methyl)urea (0.500 g, 0.8324 mmol) was dissolved in dichloromethane at room temperature and iodotrimethylsilane (0.3554 mL, 2.497 mmol) added dropwise to the stirred solution. The reaction mixture was monitored by HPLC analysis and when no starting material was detected, the mixture was diluted with dichloromethane and washed with 10% aqueous Na2S2O4, saturated aqueous NaHCO3, brine, dried (MgSO4) and concentrated under reduced pressure to afford 536 mg (quant. yield) of the crude product, which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.76 (s, 1H), 7.97 (s, 1H), 6.78-7.30 (m, 10H), 6.17 (s, 1H), 5.99 (br, 1H), 5.44 (q, 1H, J=6.1 Hz), 4.46 (m, 4H), H 2.35 (s, 3H), 1.34 (s, 9H).

Workup

  1. washwashed with 10% aqueous Na2S2O4, saturated aqueous NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de079668ea0f499eb04c111f9e6b1c0f
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044083B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes