Water → 3-[3-Bromo-4-[2-(1-pyrrolidinyl)ethoxy]benzyl]-6-hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene Dioxalate Hydrate

HRID 1070333

반응식

HRID 1070333 반응식
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]2[C:20]([C:21]([C:23]3[CH:28]=[CH:27][C:26](F)=[C:25]([Br:30])[CH:24]=3)=O)=[C:19]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][N:40]4[CH2:44][CH2:43][CH2:42][CH2:41]4)=[CH:33][CH:32]=3)[S:18][C:17]=2[CH:45]=1.[OH2:46].CN([CH:50]=[O:51])C>>[OH2:3].[C:50]([OH:51])(=[O:12])[C:4]([OH:3])=[O:46].[C:50]([OH:51])(=[O:3])[C:11]([OH:12])=[O:46].[Br:30][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[O:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:21][C:20]1[C:16]2[CH:15]=[CH:14][C:13]([OH:12])=[CH:45][C:17]=2[S:18][C:19]=1[C:31]1[CH:32]=[CH:33][C:34]([O:37][CH2:38][CH2:39][N:40]2[CH2:41][CH2:42][CH2:43][CH2:44]2)=[CH:35][CH:36]=1

참가 물질

6

반응물 5

HCID 962WaterHCID 6228Dimethylformamide2회HCID 24758Sodium hydrideHCID 762881-PyrrolidineethanolHCID 211829863-Bromo-4-fluorophenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone

생성물 1

HCID 211827573-[3-Bromo-4-[2-(1-pyrrolidinyl)ethoxy]benzyl]-6-hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene Dioxalate Hydrate수율 10%

실험 절차

Sodium hydride (95 mg of a 60% suspension in mineral oil; 2.4 mmol) was suspended in 2 mL of DMF in a flame-dried, argon-filled flask and stirred for about 5 min. 1-(2-Hydroxyethyl)pyrrolidine (0.23 mL; 2.0 mmol) was added and the mixture was stirred for 15 min. 3-Bromo-4-fluorophenyl 6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl ketone in 3 mL of DMF was then added. The mixture was stirred for 4 h at room temperature, then poured into water (25 mL), and extracted with EtOAc (4×25 mL). The combined organics were washed with brine and dried over magnesium sulfate. The title compound (135 mg; 10% yield) was isolated by flash chromatography on silica gel eluting with a gradient of EtOAc(100-90%)/Et3N(0-5%)/MeOH(0-5%).

후처리

  1. additionfilled flask
  2. stirringthe mixture was stirred for 15 min
  3. stirringThe mixture was stirred for 4 h at room temperature
  4. extractionextracted with EtOAc (4×25 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over magnesium sulfate

출처 및 근거

ORD 기록
ord-ed363e9a5f86420496692ad18d0920b2
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251921B1

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