Potassium Phosphate, Tribasic → HCID 24826749, compound

HRID 911006Notes

Reaction equation

HRID 911006 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[F:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=1[O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23](Cl)[CH:22]=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>[F:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]=1[O:20][C:21]1[CH:22]=[CH:23][N:24]=[C:25]([NH:7][C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH:26]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 86634743HCID 86634743, compound

Product 1

HCID 24826749HCID 24826749, compoundYield 81.5%

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 (0.600 g, 5.26 mmol), ethyl 4-fluoro-3-(2-chloropyridin-4-yloxy)benzoate (1.55 g, 5.26 mmol), potassium phosphate (1.23 g, 5.78 mmol), Pd2(dba)3 (0.120 g, 0.131 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.084 g, 0.131 mmol) were reacted to provide ethyl 4-fluoro-3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)benzoate (1.60 g, 77% yield). 1H NMR (CDCl3) δ 10.16 (bs, 1H), 8.20 (d, 1H), 7.97 (m, 1H), 7.86 (dd, 1H), 7.26 (t, 1H), 6.48 (dd, 1H), 6.29 (d, 1H), 6.28 (d, 1H), 4.38 (q, 2H), 2.18 (s, 3H), 1.38 (t, 3H); Mass spectrum (esi) m/z 374 (100) (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ad0b4ec878e84d11be7956d882a5b0d7
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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