1,2-Dimethoxyethane → HCID 67958892, compound

HRID 1404992Notes

Reaction equation

HRID 1404992 reaction equation
Br[C:2]1[S:18][C:5]2[CH2:6][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:9][O:10][C:4]=2[C:3]=1[CH:19]1[CH2:21][CH2:20]1.[CH3:22]B(O)O.P([O-])([O-])([O-])=O.[K+].[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>[CH:19]1([C:3]2[C:4]3[O:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][C:5]=3[S:18][C:2]=2[CH3:22])[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 67959407HCID 67959407, compound

Product 1

HCID 67958892HCID 67958892, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A solution of tert-butyl 7-bromo-8-cyclopropyl-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (264 mg), methylboronic acid (169 mg), potassium phosphate (600 mg), tetrakis(triphenylphosphine)palladium (81.7 mg) and DME (3 mL) was stirred at 80° C. for 20 hr, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 2→10% ethyl acetate/hexane) to give the title compound (166 mg, 76%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (solvent gradient; 2→10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c46ea9a395164013a14fc924f3737476
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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