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Thioglycolic Acid → N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyaniline

HRID 508209
ノート
印刷プレビュー

反応式

HRID 508209 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH:17]([F:40])[CH2:18][N:19]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)S(C3C=CC([N+]([O-])=O)=CC=3)(=O)=O)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[OH-].[Li+].CN(C)C=O.SCC(O)=O>CCOC(C)=O>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:16][CH:17]([F:40])[CH2:18][NH:19][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1133Thioglycolic AcidHCID 3939Lithium HydroxideHCID 6228DimethylformamideHCID 58065896N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide

生成物 1

HCID 46853447N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyaniline収率 88%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a vial containing N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide (21.0 mg, 0.030 mmol; see representative procedure 4) was added lithium hydroxide (3.2 mg, 0.134 mmol), dimethylformamide (0.5 ml, 0.06 M) and mercaptoacetic acid (4.2 ul 0.060 mmol). After stirring at rt for 1 h the reaction mixture was diluted with EtOAc and washed sequentially with water, saturated sodium bicarbonate solution, water (3×) and brine. The organic layer was dried over Na2SO4, filtered and condensed. The crude reaction mixture was purified in 30% EtOAc/hexanes (+0.2% TEA), with 13.6 mg isolated. Yield=88%

後処理

  1. washwashed sequentially with water, saturated sodium bicarbonate solution, water (3×) and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customcondensed
  5. customThe crude reaction mixture
  6. customwas purified in 30% EtOAc/hexanes (+0.2% TEA), with 13.6 mg
  7. customisolated

出典と根拠

ORDレコード
ord-f323e5b16b5249e3bfc4a7d5a49e5ca0
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09095572B2

反応ノート

読み込み中…

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