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 2190184노트

반응식

HRID 2190184 반응식
[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]

참가 물질

6

반응물 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

생성물 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 methylamide수율 56.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aa83a83bc703488e8b5779ed679ff095
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324239B2

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