Cesium carbonate → N-[[(3S,3aS)-7-(2-methylsulfonylphenyl)-1-oxo-3a,4-dihydro-3H-[1,3]oxazolo[4,3-c][1,4]benzoxazin-3-yl]methyl]-5-chlorothiophene-2-carboxamide

HRID 1050224ノート

反応式

HRID 1050224 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]2[C@H:19]3[N:14]([C:15]4[CH:23]=[CH:22][C:21](B5OC(C)(C)C(C)(C)O5)=[CH:20][C:16]=4[O:17][CH2:18]3)[C:13](=[O:33])[O:12]2)=[O:8])=[CH:4][CH:3]=1.[CH3:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1Br)(=[O:37])=[O:36].C(=O)([O-])[O-].[Cs+].[Cs+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@H:11]2[C@H:19]3[N:14]([C:15]4[CH:23]=[CH:22][C:21]([C:39]5[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=5[S:35]([CH3:34])(=[O:37])=[O:36])=[CH:20][C:16]=4[O:17][CH2:18]3)[C:13](=[O:33])[O:12]2)=[O:8])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 190318Benzene, 1-bromo-2-(methylsulfonyl)-HCID 1317360535-chloro-N-(((3S,3 aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide

生成物 1

HCID 118574663N-[[(3S,3aS)-7-(2-methylsulfonylphenyl)-1-oxo-3a,4-dihydro-3H-[1,3]oxazolo[4,3-c][1,4]benzoxazin-3-yl]methyl]-5-chlorothiophene-2-carboxamide収率 35.2%

試薬・触媒・溶媒 1

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒

実験手順

Using compound 5-chloro-N-(((3S,3aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide (the product of step (b) in Example 35) (50 mg, 0.102 mmol), o-methylsulfonylbromobenzene (29 mg, 0.122 mmol), tetrakis (triphenylphosphine) palladium (12 mg, 0.010 mmol), and cesium carbonate (66 mg, 0.204 mmol) as starting materials, preparation following the method as described in Example 35 (c) afforded off-white solid 19 mg, yield: 35.2%.

後処理

  1. custommaterials, preparation

出典と根拠

ORDレコード
ord-63b99377bf65496fbe3f2ee9b3c54596
出典データセット
uspto-grants-2016_07
特許番号
US09382265B2

反応ノート

読み込み中…