Cesium carbonate → HCID 71543462, compound

HRID 1776815Notes

Reaction equation

HRID 1776815 reaction equation
[F:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[NH:8][C:9]([C:11]3[N:16]=[C:15]([C:17]4[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:40])=[O:39])=[CH:19][C:20]5[O:24][C:23]([C:25]6[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=6)=[C:22]([C:32]([NH:34][CH3:35])=[O:33])[C:21]=5[CH:36]=4)[CH:14]=[CH:13][C:12]=3[OH:43])=[CH:10][C:3]=12.[C:44]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[F:1][C:2]1[C:3]2[CH:10]=[C:9]3[C:11]4[N:16]=[C:15]([C:17]5[C:18]([N:37]([CH3:42])[S:38]([CH3:41])(=[O:39])=[O:40])=[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]=[CH:13][C:12]=4[O:43][CH2:44][N:8]3[C:4]=2[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 136341365HCID 136341365, compound

Product 1

HCID 71543462HCID 71543462, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 5-(6-(4-fluoro-1H-pyrrolo[2,3-c]pyridin-2-yl)-5-hydroxypyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (100 mg, 0.17 mmol) and Cs2CO3 (108 mg, 0.33 mmol) in DMF (3 mL) was added chloroidomethane (35 mg, 0.2 mmol) dropwise at 100° C. under N2. The mixture was heated for 8 hours. The mixture was diluted with H2O and extracted with EtOAc. The organics were washed with brine and dried over Na2SO4. The crude product was purified using prep-HPLC to obtain the product of Compound 46 (30 mg, yield: 30%). 1H-NMR (CDCl3, 400 MHz) δ 8.61 (s, 1H), 8.17 (s, 1H), 8.05 (s, 1H), 7.95 (t, J=6.0 Hz, 2H), 7.65 (s, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.53 (d J=8.0 Hz, 1H), 7.25˜7.19 (m, 3H), 6.10 (s, 2H), 5.99 (s, 1H), 3.37 (s, 3H), 3.00 (d, J=4.0 Hz, 3H), 2.80 (s, 3H). MS (M+H)+: 616.

Workup

  1. temperatureThe mixture was heated for 8 hours
  2. extractionextracted with EtOAc
  3. washThe organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-0168223c00154a1188af7ca417bc925f
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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