Water → 4-(5-(4-(2,5-Bis(4-bromophenyl)pyrrolidin-1-yl)phenyl)pyridin-2-yl)morpholine

HRID 1471032노트

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HRID 1471032 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=3)[N:9]2[C:20]2[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:36]=[CH:37][C:38]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)=[N:39][CH:40]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH:10]([C:13]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=3)[N:9]2[C:20]2[CH:25]=[CH:24][C:23]([C:35]3[CH:36]=[CH:37][C:38]([N:41]4[CH2:42][CH2:43][O:44][CH2:45][CH2:46]4)=[N:39][CH:40]=3)=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 672380122,5-Bis(4-bromophenyl)-1-(4-iodophenyl)pyrrolidine

생성물 1

HCID 672365524-(5-(4-(2,5-Bis(4-bromophenyl)pyrrolidin-1-yl)phenyl)pyridin-2-yl)morpholine

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

The product from Example 185A (0.1 g, 0.171 mmol), 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (0.050 g, 0.171 mmol), potassium phosphate (0.028 mL, 0.343 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.570 mg, 1.715 μmol) and 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamante (1.504 mg, 5.14 μmol) were combined in THF (1.2 mL)/water (0.4 mL). The mixture was sparged with nitrogen for 15 minutes diluted into EtOAc, washed with 1M sodium bicarbonate, brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on an Isco 12 g silica cartridge eluting with 20-70% EtOAc in hexane gave the title compound as a cream colored powder (91 mg, 86%). %). MS (ESI) m/z 620 (M+H)+.

후처리

  1. customThe mixture was sparged with nitrogen for 15 minutes
  2. additiondiluted into EtOAc
  3. washwashed with 1M sodium bicarbonate, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on an Isco 12 g silica cartridge
  8. washeluting with 20-70% EtOAc in hexane

출처 및 근거

ORD 기록
ord-ed3b2b5379a14cc0927cd019b52dd87c
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006387B2

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