Potassium Phosphate, Tribasic → HCID 86661230, compound

HRID 1918876Notes

Reaction equation

HRID 1918876 reaction equation
Br[C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:12]=[N:13][N:14]([CH2:16][CH2:17][OH:18])[CH:15]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[C:19]([O:22][CH2:23][C:24]1[C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][CH:27]=[CH:26][C:25]=1[N:39]1[CH2:51][CH2:50][N:42]2[C:43]3[CH2:44][CH2:45][CH2:46][CH2:47][C:48]=3[CH:49]=[C:41]2[C:40]1=[O:52])(=[O:21])[CH3:20].CC(O[Na])=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC#N.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[C:19]([O:22][CH2:23][C:24]1[C:25]([N:39]2[CH2:51][CH2:50][N:42]3[C:43]4[CH2:44][CH2:45][CH2:46][CH2:47][C:48]=4[CH:49]=[C:41]3[C:40]2=[O:52])=[CH:26][CH:27]=[CH:28][C:29]=1[C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:12]=[N:13][N:14]([CH2:16][CH2:17][OH:18])[CH:15]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1)(=[O:21])[CH3:20]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 580438772-(2-(Acetoxymethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-oneHCID 86661229HCID 86661229, compoundHCID 178418247HCID 178418247, compound

Product 1

HCID 86661230HCID 86661230, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 140a (595 mg, 1.9 mmol), 2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate 114a (882 mg, 1.9 mmol), CH3COONa (309 mg, 3.8 mmol), PdCl2(dppf) (153 mg, 0.19 mmol) and K3PO4 (1 g, 3.8 mmol) suspended in CH3CN (30 mL) and H2O (2 mL) was heated at 110° C. for 15 h under argon atmosphere. After reaction CH3CN was evaporated and the residue was purified by reverse phase Combi-flash eluting with 0.3% NH4HCO3 in 1:4 water/CH3CN to give 140b as a brown solid (477 mg, 44%). LCMS: [M+H]+572.

Workup

  1. customwas evaporated
  2. customthe residue was purified by reverse phase Combi-flash
  3. washeluting with 0.3% NH4HCO3 in 1:4 water/CH3CN

Sources & evidence

ORD record
ord-2110ca1a15b2424daf00a84ca976ab05
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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