Cesium carbonate → HCID 77845847, compound

HRID 595686Notes

Reaction equation

HRID 595686 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]1[N:16]=[C:15]([C:17]3[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:40])=[O:39])=[CH:19][C:20]4[O:24][C:23]([C:25]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)=[C:22]([C:32]([NH:34][CH3:35])=[O:33])[C:21]=4[CH:36]=3)[CH:14]=[N:13][C:12]=1[CH:43]=[CH2:44])[NH:6]2.C([O-])([O-])=O.[Cs+].[Cs+]>Cl.O1CCOCC1.CN(C=O)C>[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:11]4[N:16]=[C:15]([C:17]5[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:40])=[O:39])=[CH:19][C:20]6[O:24][C:23]([C:25]7[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=7)=[C:22]([C:32]([NH:34][CH3:35])=[O:33])[C:21]=6[CH:36]=5)[CH:14]=[N:13][C:12]=4[CH2:43][CH2:44][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 90333585HCID 90333585, compound

Product 1

HCID 77845847HCID 77845847, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-(6-(4-fluoro-1H-indol-2-yl)-5-vinylpyrazin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (50 mg, 0.08 mmol) in HCl/1,4-dioxane (1 mL) was stirred at 80° C. for 1 h under nitrogen atmosphere. The reaction mixture was concentrated; then the residue was used to the next step reaction without purification. To the residue in DMF, Cs2CO3 was added (53 mg, 0.16 mmol), the reaction mixture was stirred at 80° C. for 1 h under nitrogen atmosphere, concentrated and purified by prep-TLC (PE:EA=1:2) to give the desired product (10 mg, yield: 20%). 1H-NMR (CDCl3, 400 MHz) δ 8.56 (s, 1H), 8.03 (s, 1H), 7.90 (dd, J=9.2 Hz, 5.2 Hz, 2H), 7.64 (s, 1H), 7.29 (s, 1H), 7.09˜7.17 (m, 4H), 6.74˜6.78 (m, 1H), 5.85 (br s, 1H), 4.41 (t, J=6.8 Hz, 2H), 3.47 (t, J=6.8 Hz, 2H), 3.34 (s, 3H), 2.94 (d, J=4.8 Hz, 3H), 2.73 (s, 3H). MS (M+H)+: 614.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthen the residue was used to the next step reaction without purification
  3. concentrationconcentrated
  4. custompurified by prep-TLC (PE:EA=1:2)

Sources & evidence

ORD record
ord-cac9ba0e01b7427ab12d6687f8d7ef1f
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

Loading…