Thiophenol → 2-(4-Fluoro-phenyl)-10-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide

HRID 2190184ノート

反応式

HRID 2190184 の反応式
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]3[C:14](=[CH2:36])[CH2:15][N:16](S(C4C=CC=CC=4[N+]([O-])=O)(=O)=O)[CH2:17][CH2:18][N:19]([S:20]([CH3:23])(=[O:22])=[O:21])[C:10]3=[N:9][C:8]=2[O:7][C:6]=1[C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].C1(S)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]3[C:14](=[CH2:36])[CH2:15][NH:16][CH2:17][CH2:18][N:19]([S:20]([CH3:23])(=[O:22])=[O:21])[C:10]3=[N:9][C:8]=2[O:7][C:6]=1[C:37]1[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=1)=[O:4]

参加物

6

反応物 4

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 666635422-(4-Fluoro-phenyl)-10-methanesulfonyl-5-methylene-7-(2-nitro-benzenesulfonyl)-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide

生成物 1

HCID 666644732-(4-Fluoro-phenyl)-10-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide収率 56.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-(4-Fluoro-phenyl)-10-methanesulfonyl-5-methylene-7-(2-nitro-benzenesulfonyl)-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide (4 mg, 7.94 umol) is dissolved in anhydrous THF (0.5 mL) and to this solution Cs2CO3 (25.9 mg, 0.08 mmol) followed by PS-thiophenol (Cardullo et. al Synlett 2005) (100 mg of resin with a 2 mmol/g of loading). This amount of resin is previously treated by shaking for 30 min in a sealed vial with 2 mL of a 0.7M solution of PPh3 in dry deoxygenated THF. The resin is filtered on a sintered glass, washed with dry THF and then used immediately without drying. The mixture is then stirred slowly overnight. The solid is filtered then washed several times with THF (25 mL) and CH2Cl2 (20 mL). The combined organic is evaporated to afford 2-(4-Fluoro-phenyl)-10-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide (2 mg, 56%). MS-ES [M+H]+=444.9.

後処理

  1. additionThis amount of resin is previously treated
  2. customin dry
  3. customdeoxygenated THF
  4. filtrationThe resin is filtered on a sintered glass
  5. washwashed with dry THF
  6. customwithout drying
  7. filtrationThe solid is filtered
  8. washthen washed several times with THF (25 mL) and CH2Cl2 (20 mL)
  9. customThe combined organic is evaporated

出典と根拠

ORDレコード
ord-aa83a83bc703488e8b5779ed679ff095
出典データセット
uspto-grants-2012_12
特許番号
US08324239B2

反応ノート

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