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

HRID 1471032ノート

反応式

HRID 1471032 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-ed3b2b5379a14cc0927cd019b52dd87c
出典データセット
uspto-grants-2015_04
特許番号
US09006387B2

反応ノート

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