Methyl 3-mercaptopropionate → HCID 86761411, compound

HRID 911079Notes

Reaction equation

HRID 911079 reaction equation
Br[C:2]1[C:3]([O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][CH:20]=[N:21]3)=[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.[SH:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30]>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>[CH3:14][C:12]1[N:13]=[C:9]([NH:8][C:5]2[N:6]=[CH:7][C:2]([S:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:3]([O:15][C:16]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:17]=3[CH:18]=[CH:19][CH:20]=[N:21]4)[CH:4]=2)[S:10][CH:11]=1

Participants

6

Reactant 2

HCID 18050Methyl 3-mercaptopropionateHCID 86634762HCID 86634762, compound

Product 1

HCID 86761411HCID 86761411, compoundYield 85.6%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
93 °C

Procedure

A flask was charged with tris(dibenzylideneacetone)dipalladium (0) (0.05539 g, 0.06049 mmol), 5-bromo-N-(4-methylthiazol-2-yl)-4-(quinolin-5-yloxy)pyridin-2-amine (0.500 g, 1.210 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.05250 g, 0.09074 mmol), methyl 3-mercaptopropanoate (0.5360 ml, 4.839 mmol), and N-ethyl-N-isopropylpropan-2-anine (0.4215 ml, 2.420 mmol), and degassed dioxane (40 mL) was added. The reaction was stirred at 93° C. overnight. Water was added and the reaction was extracted with ethyl acetate. The organic layer was dried, filtered and concentrated. The residue was purified using silica gel column chromatography with 20-30-40-60-80% ethyl acetate in hexanes and then with ethyl acetate to give the desired product (0.469 g, 85% yield) as yellow solid. 1H NMR (CDCl3) δ 8.93 (m, 1H), 8.37 (d, 1H), 8.19 (m, 1H), 8.02 (dd, 1H), 7.66 (t, 1H), 7.36 (dd, 1H), 7.19 (d, 2H), 6.11 (s, 1H), 3.60 (s, 3H), 2.60 (t, 2H), 1.71 (s, 3H), 1.22 (t, 2H).

Workup

  1. customdegassed dioxane (40 mL)
  2. additionwas added
  3. additionWater was added
  4. extractionthe reaction was extracted with ethyl acetate
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified

Sources & evidence

ORD record
ord-a9637874b8d946f9998d25657927a595
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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