Water → HCID 68689588, compound

HRID 1159040Notes

Reaction equation

HRID 1159040 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][N:11]2[C:12](=[O:24])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16](Br)=[CH:15][C:14]=3[C:20]([F:23])([F:22])[F:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:27](/B(O)O)=[CH:28]/[CH3:29].C(=O)([O-])[O-].[K+].[K+].O>COCCOC.[Cl-].[Na+].O.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:1]([O:5][C:6]([N:8]1[CH2:26][CH2:25][N:11]2[C:12](=[O:24])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16](/[CH:27]=[CH:28]\[CH3:29])=[CH:15][C:14]=3[C:20]([F:23])([F:22])[F:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 16115648HCID 16115648, compound

Product 1

HCID 68689588HCID 68689588, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring degassed solution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-bromo-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (54 mg, 0.12 mmol) in DME (1.2 mL) was added tetrakis(triphenylphosphine)palladium(0) (1.7 mg, 0.0015 mmol). After 15 min., cis-1-propenylboronic acid (31 mg, 0.37 mmol), potassium carbonate (17 mg, 0.12 mmol), and water (0.3 mL) were added. The reaction was heated to reflux for 3 h and then cooled to room temp. The reaction was diluted with brine and extracted with EtOAc (3×5 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a yellow oil. The oil was purified by flash chromatography (silica gel, 0-50% EtOAc in hexanes) to give 42 mg of the desired product as a colorless oil. MS (ESI) 397 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with EtOAc (3×5 mL)
  4. dry with materialdried over Na2SO4
  5. customThe oil was purified by flash chromatography (silica gel, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9e17236320dd4139a20939632b6beb02
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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