Potassium Phosphate, Tribasic → HCID 24825880, compound

HRID 910920Notes

Reaction equation

HRID 910920 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[Cl:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][N:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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>[ClH:8].[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:9]2[CH:14]=[C:13]([O:15][C:16]3[C:25]4[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=4[CH:19]=[CH:18][CH:17]=3)[CH:12]=[CH:11][N:10]=2)[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 86634719HCID 86634719, compound

Product 1

HCID 24825880HCID 24825880, compoundYield 45.4%

Reagents, catalysts & solvents 2

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

Procedure

Using the method of Example 3, Step B, 4-methylthiazol-2-amine (16.77 mL, 6.708 mmol), 2-chloro-4-(5,6,7,8-tetrahydronaphthalen-1-yloxy)pyridine (1.584 g, 6.099 mmol), potassium phosphate (1.424 g, 6.708 mmol), Pd2(dba)3 (0.1396 g, 0.1525 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.09528 g, 0.1647 mmol) were reacted to provide N-(4-methylthiazol-2-yl)-4-(5,6,7,8-tetrahydronaphthalen-1-yloxy)pyridin-2-amine hydrochloride (1.035 g, 45.39% yield) after salt formation. 1H NMR (d6-DMSO) δ 8.23 (d, 1H), 7.24 (t, 1H), 7.09 (d, 1H), 6.96 (d, 1H), 6.69 (s, 1H), 6-65 (m, 1H), 6.54 (m, 1H), 2.79 (m, 2H), 2.48 (m, 2H), 2.25 (s, 3H), 1.70 (m, 4H); Mass spectrum (apci) m/z=338.2 (M+H—HCl).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e7996cdc1b07481898b3c4e544eb39e6
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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