Dimethylformamide → HCID 59799040, compound

HRID 911236Notes

Reaction equation

HRID 911236 reaction equation
C([CH:4]1[C:10]2[C:11](Br)=[CH:12][CH:13]=[C:14]([OH:15])[C:9]=2[CH2:8][CH2:7][N:6]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:5]1)(=O)C.[CH:23]([O-:25])=O.[Na+].[CH3:27]N(C=O)C>CCOC(C)=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:23]([C:13]1[CH:12]=[CH:11][C:10]2[CH2:4][CH2:5][N:6]([C:17](=[O:22])[C:18]([F:20])([F:19])[F:21])[CH2:7][CH2:8][C:9]=2[C:14]=1[OH:15])(=[O:25])[CH3:27]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 2723810Sodium FormateHCID 86761412HCID 86761412, compound

Product 1

HCID 59799040HCID 59799040, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Mix-acetyl-9-bromo-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (833 mg, 2.2 mmol), tetrakis(triphenylphosphine)palladium(0) (150 mg, 0.13 mmol) and sodium formate (224 mg, 3.3 mmol) in anhydrous DMF (15 mL). Degas twice then flush with argon. Keep the flask under argon and heat the reaction at 95° C. for 16 h. Dilute with EtOAc then wash with 1N aqueous HCl. Separate the organic layer, dry over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with EtOAc/hexane (0:1, 1:9 and 1:4) to give the desired intermediate (448 mg, 68%). MS (ES+) m/z: 302 (+H)+.

Workup

  1. customDegas twice
  2. customthen flush with argon
  3. temperatureheat
  4. customthe reaction at 95° C. for 16 h
  5. washthen wash with 1N aqueous HCl
  6. customSeparate the organic layer
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customPurify by chromatography on silica gel eluting with EtOAc/hexane (0:1, 1:9 and 1:4)

Sources & evidence

ORD record
ord-00bd45ac40ee49fd89c039e74e3aa003
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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