Toluene → Ethyl 6-(4-isopropylthiazol-2-ylamino)-4-phenoxynicotinate

HRID 910967

反応式

HRID 910967 の反応式
Cl[C:2]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[CH:20]([C:23]1[N:24]=[C:25]([NH2:28])[S:26][CH:27]=1)([CH3:22])[CH3:21].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].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>[CH:20]([C:23]1[N:24]=[C:25]([NH:28][C:2]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=2)[S:26][CH:27]=1)([CH3:22])[CH3:21]

参加物

8

反応物 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 70640774-(Propan-2-yl)-1,3-thiazol-2-amineHCID 54487232Ethyl 6-chloro-4-phenoxynicotinate

生成物 1

HCID 24826427Ethyl 6-(4-isopropylthiazol-2-ylamino)-4-phenoxynicotinate収率 82.5%

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒

実験手順

Using the method of Example 3, Step B, ethyl 6-chloro-4-phenoxynicotinate (4.296 g, 15.47 mmol), 4-isopropylthiazol-2-amine (2 g, 14.06 mmol), potassium phosphate (3.283 g, 15.47 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.3219 g, 0.3516 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.2238 g, 0.3867 mmol) were reacted in water (15 mL) and toluene (40 mL) to afford the desired product (4.447 g, 74.22% yield) as a yellow solid. 1H NMR (DMSO), 11.36 (s, 1H), 8.72 (s, 1H), 7.49 (m, 2H), 7.30 (m, 1H), 7.17 (m, 1H), 7.15 (m, 1H), 6.59 (m, 2H), 4.24 (q, 2H), 2.81 (m, 1H), 1.25 (t 3H), 1.15 (d, 6H); Mass spectrum (apci) m/z=384 (100) (M+H).

出典と根拠

ORDレコード
ord-f3f5208676ac4c7992cd47bf801ad103
出典データセット
uspto-grants-2011_09
特許番号
US08022222B2

関連ノート

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