Water → HCID 86649119, compound

HRID 1471033Notes

Reaction equation

HRID 1471033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C@H:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=3)[N:9]2[C:23]2[CH:28]=[CH:27][CH:26]=[C:25](I)[CH:24]=2)=[CH:4][C:3]=1[N+:30]([O-:32])=[O:31].CC1(C)C(C)(C)OB([C:41]2[CH:42]=[CH:43][C:44]([N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)=[N:45][CH:46]=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]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C@H:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=3)[N:9]2[C:23]2[CH:24]=[C:25]([C:41]3[CH:42]=[CH:43][C:44]([N:47]4[CH2:48][CH2:49][O:50][CH2:51][CH2:52]4)=[N:45][CH:46]=3)[CH:26]=[CH:27][CH:28]=2)=[CH:4][C:3]=1[N+:30]([O-:32])=[O:31]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 86649120HCID 86649120, compound

Product 1

HCID 86649119HCID 86649119, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 187A (1.4 g, 2.396 mmol), 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (0.695 g, 2.396 mmol), potassium phosphate (1.017 g, 4.79 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.022 g, 0.024 mmol) and 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamante (0.021 g, 0.072 mmol) were combined in THF (18 mL)/water (6 mL). The mixture was sparged with nitrogen for 15 minutes, stirred for 6 hours diluted into EtOAc, washed with 1M sodium bicarbonate, brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on an Isco 120 g silica cartridge eluting with 20-60% EtOAc in hexane gave the title compound as a yellow glass (1.1 g, 74%). MS (ESI) m/z 620 (M+H)+.

Workup

  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 120 g silica cartridge
  8. washeluting with 20-60% EtOAc in hexane

Sources & evidence

ORD record
ord-1dff9081f2494d8bae507fd9413278b5
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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