HCID 86761651, compound → HCID 68483867, compound

HRID 1875076Notes

Reaction equation

HRID 1875076 reaction equation
[N:1]([C:4]1[N:5]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:6]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[C:16]([O:21][C:22]3[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[C:24]([Cl:30])[CH:23]=3)[C:15]=2[F:31])=[O:11])=[C:7]([Br:9])[N:8]=1)=[N+]=[N-]>C1COCC1.[Pd]>[NH2:1][C:4]1[N:5]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:6]([C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[C:16]([O:21][C:22]3[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[C:24]([Cl:30])[CH:23]=3)[C:15]=2[F:31])=[O:11])=[C:7]([Br:9])[N:8]=1

Participants

4

Reactant 1

HCID 86761651HCID 86761651, compound

Product 1

HCID 68483867HCID 68483867, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-azido-4-bromo-N-({4-bromo-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (0.030 g, 0.043 mmol) and catalytic palladium on Ca2CO3 (poisoned with lead) in THF (1 mL) was stirred under atmospheric hydrogen pressure overnight. The reaction mixture was filtered through celite and evaporated to give the title compound (0.029 mg, quant.) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.43 (dd, J=8.47, 1.42 Hz, 1H) 7.31-7.37 (m, 1H) 7.21-7.26 (m, 1H) 7.11-7.17 (m, 1H) 7.06 (t, J=6.00 Hz, 1H) 7.01 (s, 1H) 5.69 (s, 2H) 4.85 (br. s., 2H) 4.63 (d, J=6.04 Hz, 2H) 3.59-3.68 (m, 2H) 0.86-0.94 (m, 2H) −0.03 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-bbbc5e10add5463981f60396813d3b98
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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