HCID 24738993, compound → HCID 86613884, compound

HRID 731650Notes

Reaction equation

BrC1C=CC2N(C=C(C3C(C4C=CC=CC=4)=NOC=3C)N=2)C=1.[CH3:23][C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]=1[C:35]1[N:36]=[C:37]2[CH:42]=[CH:41][C:40]([C:43]#[C:44][Si](C)(C)C)=[CH:39][N:38]2[CH:49]=1>>[C:43]([C:40]1[CH:41]=[CH:42][C:37]2[N:38]([CH:49]=[C:35]([C:25]3[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:27][O:28][C:24]=3[CH3:23])[N:36]=2)[CH:39]=1)#[CH:44]

Participants

Reactant 2

HCID 24738993HCID 24738993, compound

HCID 69062632HCID 69062632, compound

Product 1

HCID 86613884HCID 86613884, compoundYield 69%

Procedure

As described for Example 45, 6-bromo-2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridine (100 mg, 0.28 mmol) instead of 7-bromo-2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridine, was converted to 2-(5-methyl-3-phenyl-isoxazol-4-yl)-6-trimethylsilanylethynyl-imidazo[1,2-a]pyridine (39 mg, 37% MS: m/e=372.1 [M+H]+) and then to the title compound (19 mg, 69%) which was obtained as a light yellow foam. MS: m/e=300.3 [M+H]+.

Sources & evidence

ORD record: ord-ab73d1909a3f42c793cf5c80730b5d6d
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585874B2

Reaction notes

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