Cesium carbonate → tert-butyl 4-[6-(1,3-benzodioxol-5-yl)-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

HRID 1476628ノート

反応式

HRID 1476628 の反応式
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:6](=[O:25])[N:5]([CH2:26][C:27]3[O:31][N:30]=[C:29]([CH2:32][CH3:33])[N:28]=3)[C:4]=2[CH:3]=1.[O:34]1[C:38]2[CH:39]=[CH:40][C:41](B(O)O)=[CH:42][C:37]=2[O:36][CH2:35]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl>[O:34]1[C:38]2[CH:39]=[CH:40][C:41]([C:2]3[S:10][C:9]4[C:8](=[O:11])[N:7]([CH:12]5[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:16][CH2:17]5)[C:6](=[O:25])[N:5]([CH2:26][C:27]5[O:31][N:30]=[C:29]([CH2:32][CH3:33])[N:28]=5)[C:4]=4[CH:3]=3)=[CH:42][C:37]=2[O:36][CH2:35]1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 67258967Tert-butyl 4-{6-bromo-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate

生成物 1

HCID 67258594tert-butyl 4-[6-(1,3-benzodioxol-5-yl)-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)触媒HCID 312751,4-Dioxane溶媒

実験手順

Tert-butyl 4-{6-bromo-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate 405 mg, compound B99), 1,3-benzodioxol-5-ylboronic acid (368 mg), dichlorobis(tricyclohexylphosphine)palladium (137 mg) and aqueous cesium carbonate solution (1.39 ml, 2.0 M) in dioxane (18 ml) are reacted according to the procedure described in example B55 to afford the title compound after purification by flash column chromatography [silica gel, elution gradient: cyclohexane/EtOAc, 80/20 to 50/50 (v/v)] as a solid.

出典と根拠

ORDレコード
ord-089b51ce96244c02accf7011999c5a56
出典データセット
uspto-grants-2015_04
特許番号
US09018175B2

反応ノート

読み込み中…