Sodium Formate → HCID 59799040, compound

HRID 1013109Notes

Reaction equation

HRID 1013109 reaction equation
[C:1]([C:4]1[CH:20]=[C:19](Br)[C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:11][CH2:12][C:6]=2[C:5]=1[OH:22])(=[O:3])[CH3:2].C([O-])=O.[Na+]>CN(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:1]([C:4]1[CH:20]=[CH:19][C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:17])([F:15])[F:16])[CH2:11][CH2:12][C:6]=2[C:5]=1[OH:22])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 2723810Sodium FormateHCID 57447750HCID 57447750, compound

Product 1

HCID 59799040HCID 59799040, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix 7-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 1 N HCl. Separate the organic layer, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 1:100 to 20:80 EtOAc:hexanes) to give the title compound (448 mg, 68%).

Workup

  1. customDegas twice
  2. customthen flush with argon
  3. temperatureheat
  4. customthe reaction at 95° C. for 16 h
  5. washthen wash with 1 N HCl
  6. customSeparate the organic layer
  7. dry with materialdry (sodium sulfate)
  8. concentrationconcentrate
  9. custompurify
  10. wash(silica gel chromatography, eluting with 1:100 to 20:80 EtOAc:hexanes)

Sources & evidence

ORD record
ord-9471506e2b3f4276b41cacd3a92e59c8
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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