Methyl 3-mercaptopropionate → Methyl 3-(2-(thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-ylthio)propanoate

HRID 335177Notes

Reaction equation

Br[C:2]1[C:3]([NH:8][C:9]2[S:10][C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:4][CH:5]=[CH:6][CH:7]=1.[SH:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22].C(N(C(C)C)C(C)C)C.O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(OCC)(=O)C>[N:17]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[S:10][C:9]=1[NH:8][C:3]1[C:2]([S:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of N-(3-bromopyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine (0.55 g, 1.79 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.052 g, 0.090 mmol), Pd2dba3 (0.041 g, 0.045 mmol), methyl 3-mercaptopropanoate (0.21 mL, 1.88 mmol), N-ethyl-N-isopropylpropan-2-amine (0.62 mL, 3.60 mmol), and dioxane (40 mL) was heated to 95° C. under nitrogen. Cooled to ambient temperature and filtered the solids. Concentrated and purified by MPLC (Biotage) eluting with 1:1 hexane:ethyl acetate to afford the title compound (0.541 g, 87% yield) as a dark yellow oil.

Workup

temperatureCooled to ambient temperature
filtrationfiltered the solids
concentrationConcentrated
custompurified by MPLC (Biotage)
washeluting with 1:1 hexane

Sources & evidence

ORD record: ord-4552770fe4b74bea91f4f80720d01eba
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883828B2

Reaction notes

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