Cesium carbonate → HCID 57431683, compound

HRID 545584Notes

Reaction equation

HRID 545584 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([C:5]1[CH:6]=[C:7]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]1[CH2:12][CH2:11][CH:10]([NH:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH2:9][C:8]2=1)=[O:4].[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][N:14]1[C:13]2[CH2:12][CH2:11][CH:10]([NH:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH2:9][C:8]=2[C:7]2[C:15]1=[CH:16][CH:17]=[C:5]([C:3](=[O:4])[C:2]([F:1])([F:24])[F:25])[CH:6]=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680073-Fluorobenzyl bromideHCID 57431682HCID 57431682, compound

Product 1

HCID 57431683HCID 57431683, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Mix N-[6-(2,2,2-trifluoro-acetyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Preparation 74) (428 mg, 0.93 mmol), m-fluorobenzyl bromide (216 mg, 1.11 mmol), Cs2CO3 (650 mg, 2 mmol) and DMF (10 mL). Warm the reaction at 50° C. for 18 h, cool and partition between water/brine/EtOAc. Separate and dry the organic layer (MgSO4), filter and concentrate to give 590 mg of crude product. Purify by silica gel chromatography, using 10% to 60% EtOAc/hexane to obtain 68 mg (16%) of the title compound as a pale yellow solid. MS (ES) m/z 461 (M+1); HPLC: Rt=3.43 min (95%).

Workup

  1. temperatureWarm
  2. customthe reaction at 50° C. for 18 h
  3. temperaturecool
  4. custompartition between water/brine/EtOAc
  5. customSeparate
  6. dry with materialdry the organic layer (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate
  9. customto give 590 mg of crude product
  10. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-72b4014c956a41b493c78fb5f4c25021
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

Loading…