Methyl iodide → HCID 22477179, compound

HRID 2182224Notes

Reaction equation

HRID 2182224 reaction equation
[CH3:1]I.[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[N:17]([Sn](C)(C)C)[N:16]=[N:15][N:14]=3)=[CH:10][CH:11]=2)[C:6]([C:22]2[N:30]([S:31]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[C:25]3=[N:26][CH:27]=[CH:28][CH:29]=[C:24]3[CH:23]=2)=[CH:5]1>O>[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[N:17]([CH3:1])[N:16]=[N:15][N:14]=3)=[CH:10][CH:11]=2)[C:6]([C:22]2[N:30]([S:31]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[C:25]3=[N:26][CH:27]=[CH:28][CH:29]=[C:24]3[CH:23]=2)=[CH:5]1.[CH3:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[N:17]=[N:16][N:15]([CH3:1])[N:14]=3)=[CH:10][CH:11]=2)[C:6]([C:22]2[N:30]([S:31]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[C:25]3=[N:26][CH:27]=[CH:28][CH:29]=[C:24]3[CH:23]=2)=[CH:5]1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 22477642HCID 22477642, compound

Product 2

HCID 22477179HCID 22477179, compoundHCID 22477199HCID 22477199, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl iodide (2.5 mL) was added to a solution of 2-[1-methyl-5-(1-trimethylstannanyl-1H-tetrazol-5-yl)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [620 mg, Reference Example 20] at ambient temperature. The mixture was then allowed to stir at ambient temperature for 4 hours then was poured into water and then extracted with ethyl acetate. The combined extract was washed with brine, then dried over magnesium sulfate and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petroleum ether (1:1, v/v) to give 2-[1-methyl-5-(1-methyl-1H-tetrazol-5-yl)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (191 mg) as a colourless solid, [MS: 506(MNa+). 1H NMR [(CD3)2SO]: δ 8.39 (dd, 1H, J=4.8 and 1.6 Hz); 7.97 (m, 1H); 7.96 (d, 1H, J=4.0 Hz); 7.90 (s, 1H); 7.80 (dd, 1H, J=8.7 and 0.6 Hz); 7.70 (dd, 1H, J=8.7 and 1.8 Hz); 7.56 (m, 2H); 7.30 (dd, 1H, J=7.7 and 4.8 Hz); 7.22 (m, 2H); 6.82 (s, 1H); 4.19 (s, 3H); 4.0 (s, 3H); 2.23 (s, 3H)] and 2-[1-Methyl-5-(2-methyl-2H-tetrazol-5-yl)-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (77 mg) as a colourless solid, m.p. 215-218° C. [MS: 506(MNa+)].

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe combined extract
  3. washwas washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petroleum ether (1:1

Sources & evidence

ORD record
ord-05e5c2a1adbc48df8504795501defe62
Source dataset
uspto-grants-2005_05
Patent number
US06897207B2

Reaction notes

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