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1,2-Dimethoxyethane → HCID 68578117, compound

HRID 886980
Notes
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Reaction equation

HRID 886980 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([F:20])=[C:18](Br)[C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:21]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22]1.C(=O)([O-])[O-].[K+].[K+].COCCOC>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.O>[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([F:20])=[C:18]([C:23]3[CH:24]=[CH:25][O:21][CH:22]=3)[C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2734358Furan-3-boronic acidHCID 68577855HCID 68577855, compound

Product 1

HCID 68578117HCID 68578117, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 4-benzyl-9-bromo-8-fluoro-2,3,4,5-tetrahydro-1,4-benzoxazepine (500 mg, 1.49 mmol), 3-furanboronic acid (250 mg, 2.23 mmol), potassium carbonate (206 mg, 1.49 mmol), tetrakis(triphenylphosphine)palladium(0) (172 mg, 0.149 mmol), 1,2-dimethoxyethane (5 ml) and water (0.5 ml) was stirred under an argon atmosphere at 100° C. for 3 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) and preparative HPLC to give the desired product (104 mg, 21.7%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) and preparative HPLC

Sources & evidence

ORD record
ord-134229a496b74a4e871f568235b70f08
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08247403B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes