Tributylvinyltin → 3-Phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)isoxazole

HRID 1506482ノート

反応式

HRID 1506482 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[S:10][C:9]([C:15]3[O:19][N:18]=[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:16]=3[C:26]([F:29])([F:28])[F:27])=[N:8][C:7]=1[CH2:6][CH2:5]2.[CH2:30]([Sn](CCCC)(CCCC)C=C)[CH2:31]CC>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:20]1([C:17]2[C:16]([C:26]([F:27])([F:28])[F:29])=[C:15]([C:9]3[S:10][C:11]4[C:12]5[C:4](=[CH:3][C:2]([CH:30]=[CH2:31])=[CH:14][CH:13]=5)[CH2:5][CH2:6][C:7]=4[N:8]=3)[O:19][N:18]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 2

HCID 81998TributylvinyltinHCID 671714645-(7-Bromo-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole

生成物 1

HCID 671705843-Phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)isoxazole

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To 5-(7-bromo-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole (Preparation 82D), 0.4 g, 0.838 mmol) in toluene (2 mL) was added tributyl(vinyl)stannane (0.294 mL, 1.00 mmol), followed by bis(triphenylphosphine)palladium(II)chloride (0.029 g, 0.042 mmol) at room temperature. The reaction mixture was heated at 110° C. for 3 h. The reaction mixture was loaded onto a silica gel column and purified using hexane/EtOAc (9.25:0.75, 300 mL). The desired fractions were collected and concentrated to yield 0.35 mgs of a yellow solid. The solid was triturated with acetonitrile (5 mL), filtered and washed with acetonitrile (2×5 mL) to yield 200 mgs of a pale yellow solid (I crop). The mother liquor was concentrated to yield another 100 mgs of greenish-yellow solid (II crop). LC/MS M+1=425.

後処理

  1. custompurified
  2. customThe desired fractions were collected
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-3561ef5ca0a9453da1a53b9ee7c48399
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

読み込み中…