Dibutyltin oxide → HCID 178519743, compound

HRID 2210611Notes

Reaction equation

HRID 2210611 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([C:26]6[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=6)=[CH:23][CH:24]=5)[N:19]([CH2:33][C:34]#[N:35])[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1.C([Sn](=O)CCCC)CCC.C[Si]([N:50]=[N+:51]=[N-:52])(C)C>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([C:26]6[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=6)=[CH:23][CH:24]=5)[N:19]([CH2:33][C:34]5[NH:52][N:51]=[N:50][N:35]=5)[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 19379099HCID 19379099, compound

Product 1

HCID 178519743HCID 178519743, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3(pyridin-3-yl)-7-[1-cyanomethyl-6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole (77 mg, 0.161 mmol), prepared as in Example 94, dibutyltin oxide (40 mg, 0.161 mmol), and trimethylsilylazide (47.3 μL, 0.322 mmol) in toluene (15 mL) was heated at reflux for three hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The crude product was azeotroped with CH2Cl2 and purified by flash chromatography on silica gel (9:1 CHCl3, methanol) to give 3-(Pyridin-3-yl)-7-[1-(1H-tetrazol-5-ylmethyl)-6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole (53 mg), m.p. 110°-118° C. 1H NMR (D3COD, 300 MHz) δ45 (d; 1H, J=15 Hz), 4.63 (dd, 1H, 15, 3 Hz), 5.75 (s, 2H), 6.57 (d, 1H, J=3 Hz), 6.67 (bs, 1H), 6.98 (d, 1H, J=3 Hz, 7.15 (t, 2H, J=9 Hz), 7.45-7.51 (m, 2H), 7.67-7.77 (m, 3H), 7.79 (s, 1H), 8.25 (s, 1H), 8.31 (d, 1H, 9 Hz), 8.55 (bs, 2H). MS (FAB) m/e 522 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for three hours
  3. concentrationconcentrated in vacuo
  4. customThe crude product was azeotroped with CH2Cl2
  5. custompurified by flash chromatography on silica gel (9:1 CHCl3, methanol)

Sources & evidence

ORD record
ord-d4b14445d4f040139ae94917606cec87
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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