o-Chlorothiophenol → 3-(benzyloxy)-5-(2-chlorophenylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride

HRID 1426137Notes

Reaction equation

HRID 1426137 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH3:22])[N:21]=2)=[N:11][CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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.[Cl:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][C:76]=1[SH:81]>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]>[ClH:74].[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH3:22])[N:21]=2)=[N:11][CH:12]=[C:13]([S:81][C:76]2[CH:77]=[CH:78][CH:79]=[CH:80][C:75]=2[Cl:74])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 80599o-ChlorothiophenolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 16061466HCID 16061466, compound

Product 1

HCID 866396843-(benzyloxy)-5-(2-chlorophenylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochlorideYield 31.6%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.125 g, 0.332 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.0192 g, 0.0332 mmol), Pd2dba3 (0.0152 g, 0.0166 mmol), N-ethyl-N-isopropylpropan-2-amine (0.116 mL, 0.664 mmol), 2-chlorobenzenethiol (0.048 g, 0.3322 mmol) were reacted according to Example 42 to provide 3-(benzyloxy)-5-(2-chlorophenylthio)-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (0.025 g, 17.10% yield) after salt formation. 1H NMR (DMSO-d6) δ 8.04 (d, 1H), 7.62 (d, 1H), 7.54 (m, 2H), 7.50 (m, 1H), 7.37 (m, 3H), 7.20 (m, 2H), 6.77 (s, 1H), 6.73 (m, 1H), 5.32 (s, 2H), 2.30 (s, 3H). Mass spectrum (apci) m/z=440.0 (M+H-HCl).

Sources & evidence

ORD record
ord-aa6457aa4c4847929d8ba2916b10ed63
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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