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Allyltributylstannane → 4-(2-allyl-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

HRID 528595
ノート
印刷プレビュー

反応式

HRID 528595 の反応式
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[C:19]([S:22]([N:25]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[C:26]3[S:27][CH:28]=[CH:29][N:30]=3)(=[O:24])=[O:23])[CH:20]=[CH:21][C:13]1=2.[CH2:40]([Sn](CCCC)(CCCC)CCCC)[CH:41]=[CH2:42]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:42]([C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][O:15][C:14]2[CH:18]=[C:19]([S:22]([N:25]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[C:26]3[S:27][CH:28]=[CH:29][N:30]=3)(=[O:24])=[O:23])[CH:20]=[CH:21][C:13]1=2)[CH:41]=[CH2:40]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 90628AllyltributylstannaneHCID 897614134-(2-bromo-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

生成物 1

HCID 897620874-(2-allyl-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide収率 96%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A reaction vial was charged with 4-(2-bromo-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (EXAMPLE 53, Step 1; 0.347 g, 0.542 mmol) and Pd(PPh3)4 (0.031 g, 0.027 mmol), and then diluted with DMF (1.084 ml). After purging with nitrogen, allyltributyltin (0.202 ml, 0.650 mmol) was added and the reaction was heated to 100° C. for 30 minutes until completion. The reaction was concentrated in vacuo and purified via silica-gel chromatography (12-g RediSep Gold column), eluting with 0-30% ethyl acetate in heptanes) to yield 4-(2-allyl-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.312 g, 0.519 mmol, 96% yield) as a yellow oil. m/z (ESI) 602.1 (M+H)+.

後処理

  1. customA reaction
  2. additionwas added
  3. concentrationThe reaction was concentrated in vacuo
  4. custompurified via silica-gel chromatography (12-g RediSep Gold column)
  5. washeluting with 0-30% ethyl acetate in heptanes)

出典と根拠

ORDレコード
ord-db47ff3223b546f9b0a044767b21f129
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346798B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート