Methyl 3-mercaptopropionate → HCID 24826835, compound

HRID 911018Notes

Reaction equation

Br[C:2]1[C:3]([O:15][C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.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(N(C(C)C)C(C)C)C.[SH:75][CH2:76][CH2:77][C:78]([O:80][CH3:81])=[O:79]>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].O1CCOCC1>[F:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:16]=1[O:15][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)[N:6]=[CH:7][C:2]=1[S:75][CH2:76][CH2:77][C:78]([O:80][CH3:81])=[O:79]

Participants

Conditions

Temperature: 100 °C

Procedure

A 25 mL round-bottomed flask is charged with N-(5-bromo-4-(2,6-difluorophenoxy)pyridin-2-yl)-4-methylthiazol-2-amine (398 mg, 1.00 mmol), Pd2dba3 (22.1 mg, 0.024 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (27.9 mg, 0.048 mmol), N-ethyl-N-isopropylpropan-2-amine (0.33 mL, 1.9 mmol), methyl 3-mercaptopropanoate (0.12 mL, 1.1 mmol), and dioxane (10 mL). The reaction mixture is heated at 100° C. under nitrogen for 2 hours, then cooled to room temperature, filtered and concentrated. The residue is purified via chromatography, eluting with 40% EtOAc in hexanes, to afford methyl 3-(4-(2,6-difluorophenoxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate.

Workup

temperaturecooled to room temperature
filtrationfiltered
concentrationconcentrated
customThe residue is purified via chromatography
washeluting with 40% EtOAc in hexanes

Sources & evidence

ORD record: ord-ff890f7b7869499f8c662fdab3ae2597
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022222B2

Reaction notes

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