Potassium Phosphate, Tribasic → 3-(benzyloxy)-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridin-2-amine

HRID 1426108

반응식

HRID 1426108 반응식
[CH2:1]([O:8][C:9]1[C:10](Cl)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C:17]1[N:21]=[C:20]([NH2:22])[S:19][N:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.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].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10]([NH:22][C:20]2[S:19][N:18]=[C:17]([CH3:16])[N:21]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 3506395-Amino-3-methyl-1,2,4-thiadiazoleHCID 8193743-(Benzyloxy)-2-chloropyridine

생성물 1

HCID 166603323-(benzyloxy)-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridin-2-amine수율 89.9%

시약·촉매·용매 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

3-(Benzyloxy)-2-chloropyridine (0.8393 g, 3.821 mmol), 3-methyl-1,2,4-thiadiazol-5-amine (8.684 mL, 3.474 mmol), potassium phosphate (0.8110 g, 3.821 mmol), tris(dibenzylideneacetone)dipalladium (O) (0.07952 g, 0.08684 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.05527 g, 0.09552 mmol) in toluene (8 mL) and water (3 mL) were reacted according to Example 17, Step B, to afford 3-(benzyloxy)-N-(3-methyl-1,2,4-thiadiazol-5-yl)pyridin-2-amine (0.932 g, 88.13% yield) as light yellow solid. 1H NMR (CDCl3) δ 8.9 (s, 1H), 7.97 (dd, J=1.17, 5.07 Hz, 1H), 7.37 (m, 5H), 7.15 (dd, J=1.17, 7.80 Hz, 1H), 6.89 (dd, J=5.07, 7.80 Hz, 1H), 5.09 (s, 2H), 2.47 (s, 3H). Mass spectrum (esi) m/z=299 (100) (M+H).

출처 및 근거

ORD 기록
ord-0bd94a505a0f4eafaa19dffb369fe65c
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933077B2

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