Cesium carbonate → HCID 59242732, compound

HRID 2427268Notes

Reaction equation

HRID 2427268 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[CH2:12][CH:13]([NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])[CH2:14][C:6]=3[C:5]=2[CH:4]=1)#[N:2].[F:21][C:22]1[N:27]=[C:26]([CH2:28]Br)[CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[C:1]([C:3]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:28][C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([F:21])[N:27]=3)[C:7]3[CH2:12][CH:13]([NH:15][C:16](=[O:20])[CH:17]([CH3:18])[CH3:19])[CH2:14][C:6]=3[C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 139852182-(Bromomethyl)-6-fluoropyridineHCID 67252702HCID 67252702, compound

Product 1

HCID 59242732HCID 59242732, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix (±)-N-(7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-isobutyramide (6.28 g, 18.8 mmol), 6-fluoro-2-bromomethylpyridine (3.93 g, 20.7 mmol), and Cs2CO3 (12.25 g, 37.6 mmol) in DMF (25 mL). Heat the reaction at 50° C. for 18 h. Cool, dilute with EtOAc, and wash with water (3×200 mL). Dry the organic layer (MgSO4) and concentrate to give 7.1 g crude material. Purify by silica gel chromatography (5-20% EtOAc/CH2Cl2). Obtain 4.0 g (56%) yellow-tan solid. MS (m/z): 377 (M+1), 375 (M−1).

Workup

  1. temperatureHeat
  2. customthe reaction at 50° C. for 18 h
  3. temperatureCool
  4. washwash with water (3×200 mL)
  5. dry with materialDry the organic layer (MgSO4)
  6. concentrationconcentrate
  7. customto give 7.1 g crude material
  8. customPurify by silica gel chromatography (5-20% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-99a5b1888a4f42d5a69684f5b2708c52
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

Loading…