3-Nitrophenylboronic Acid → HCID 67597186, compound

HRID 1600920Notes

Reaction equation

HRID 1600920 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C@@H:8]([OH:17])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1.[N+:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)([O-:22])=[O:21].[OH2:32].[OH2:33].O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:8]([OH:17])(=[O:33])[C:7]([OH:32])=[O:6].[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][CH2:9][C@H:8]([OH:17])[CH2:7][O:6][C:5]2[CH:18]=[CH:19][C:2]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:20]([O-:22])=[O:21])[CH:28]=3)=[CH:3][CH:4]=2)[CH:12]=1

Participants

8

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 151402Sodium Carbonate DecahydrateHCID 57014247HCID 57014247, compound

Product 1

HCID 67597186HCID 67597186, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Prepared according to the method described in Example 33a) from (2S)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.25 g), 3-nitrobenzeneboronic acid (0.194 g), sodium carbonate decahydrate (0.444 g) and tetrakis(triphenylphosphine)palladium(0) (0.022 g) in ethanol (1 ml), water (1 ml) and toluene (5 ml). Conversion to the oxalate salt upon treatment with excess saturated ethereal oxalic gave the title compound as a hygroscopic glass (0.21 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e8151dfb3d0744f0a8b755802beaf5e9
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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