Potassium trimethylsilanolate → 2-Methyl-N-[1-methyl-6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

HRID 520652Notes

Reaction equation

[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]4[N:25](S(C5C=CC(C)=CC=5)(=O)=O)[CH:26]=[CH:27][C:20]=34)[CH:16]=[C:15]3[C:11]=2[CH:12]=[N:13][N:14]3[CH3:38])=[O:8])[N:6]=1.C[Si](C)(C)[O-].[K+]>C1COCC1>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C:10]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]4[NH:25][CH:26]=[CH:27][C:20]=34)[CH:16]=[C:15]3[C:11]=2[CH:12]=[N:13][N:14]3[CH3:38])=[O:8])[N:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Methyl-N-(1-methyl-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-indazol-4-yl)-1,3-thiazole-4-carboxamide (44 mg) and potassium trimethyl silanolate (14 mg) were added to THF (2 ml). The reaction mixture was heated at 50° C. overnight. The reaction mixture was partitioned between water (20 ml) and DCM (20 ml). The solvent was removed. The residue was purified by FlashMaster silica cartridge (10 g) using a gradient of 0-100% ethylacetate in cyclohexane followed by 0-20% methanol in ethyl acetate over 30 min. The solvent was removed to give title compound, 31 mg.

Workup

customThe reaction mixture was partitioned between water (20 ml) and DCM (20 ml)
customThe solvent was removed
customThe residue was purified by FlashMaster silica cartridge (10 g)
customThe solvent was removed

Sources & evidence

ORD record: ord-453721cacc44488097686864906d661a
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09326987B2

Reaction notes

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