Water → N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)-1H-indole-6-carboxamide

HRID 2357802Notes

Reaction equation

HRID 2357802 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=2)[CH:3]=[CH:2]1.[NH2:13][CH2:14][C:15]1[N:16]=[CH:17][N:18]([C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=2)[CH:19]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.O>CN(C=O)C.CCOC(C)=O>[I:26][C:23]1[CH:22]=[CH:21][C:20]([N:18]2[CH:19]=[C:15]([CH2:14][NH:13][C:10]([C:7]3[CH:8]=[C:9]4[C:4]([CH:3]=[CH:2][NH:1]4)=[CH:5][CH:6]=3)=[O:12])[N:16]=[CH:17]2)=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 5952301H-indole-6-carboxylic acidHCID 592601094-Aminomethyl 1-(4-iodophenyl)imidazole

Product 1

HCID 66974184N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)-1H-indole-6-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of indole-6-carboxylic acid (85 mg, 0.528 mmol), 4-aminomethyl 1-(4-iodophenyl)imidazole 1-2 prepared in Example 1 (136 mg, 0.455 mmol) and TEA (0.150 mL, 1.08 mmol) in DMF (4 mL), BOP (280 mg, 0.633 mmol) was added. After the mixture was stirred at room temperature overnight, water and EtOAc were added. The organic layer was separated, washed with 5% aq. NaHCO3, dried over Na2SO4, concentrated in vacuo to give N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)-1H-indole-6-carboxamide as a crude sample, which was used in the next reaction without further purification. MS 443.0 (M+H).

Workup

  1. customThe organic layer was separated
  2. washwashed with 5% aq. NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27c8f03b952e47dd9cd1b2cafa1332e3
Source dataset
uspto-grants-2010_07
Patent number
US07763608B2

Reaction notes

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