Tributyltin Chloride → 5-{6-[3-(4-Fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo-[1,2-a]pyridin-3-yl}-2-thiophene carboxamide

HRID 1792531Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19](I)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:9]=2)=[CH:4][CH:3]=1.C([Sn](Cl)(CCCC)CCCC)CCC.Br[C:57]1[S:61][C:60]([C:62]([NH2:64])=[O:63])=[CH:59][CH:58]=1>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]4[N:17]([C:19]([C:57]5[S:61][C:60]([C:62]([NH2:64])=[O:63])=[CH:59][CH:58]=5)=[CH:20][N:21]=4)[CH:18]=3)=[CH:11][N:10]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 200 mg 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-(1,1,1-tributylstannyl)imidazo[1,2-a]-pyridine prepared from 6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 39) and tributyltin chloride by the same method as in Production Example 48, 51 mg 5-bromo-2-thiophene carboxamide, 14 mg tetrakis (triphenylphosphine)palladium and 3 mL xylene was stirred at 120° C. for 2 hours under nitrogen atmosphere. The solvent was evaporated, and the residue was purified by silica gel chromatography (ethyl acetate/methanol) to give 37 mg of the title compound as a colorless amorphous.

Workup

customThe solvent was evaporated
customthe residue was purified by silica gel chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record: ord-896734599f244f34b0c84bd5a29ad4fd
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074801B1

Reaction notes

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