Cesium carbonate → HCID 58015564, compound

HRID 422082Notes

Reaction equation

HRID 422082 reaction equation
[Br:1][C:2]1[O:10][C:9]2[CH:8]=[CH:7][N:6]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[NH:16][N:15]=[CH:14]4)[C:5](=[O:20])[C:4]=2[CH:3]=1.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O>[CH3:26][O:25][C:23](=[O:24])[CH2:22][N:16]1[C:17]2[C:13](=[CH:12][C:11]([N:6]3[CH:7]=[CH:8][C:9]4[O:10][C:2]([Br:1])=[CH:3][C:4]=4[C:5]3=[O:20])=[CH:19][CH:18]=2)[CH:14]=[N:15]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetate3×HCID 58015551HCID 58015551, compound

Product 1

HCID 58015564HCID 58015564, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-bromo-5-(1H-indazol-5-yl)furo[3,2-c]pyridin-4(5H)-one (1.13 g, 3.41 mmol) in DMSO (10.5 mL) was added methyl bromoacetate (0.64 mL, 6.8 mmol) and Cs2CO3 (4.44 g, 13.6 mmol). The reaction mixture was stirred at ambient temperature for 18 h; then additional methyl bromoacetate (0.30 mL) was added. After 3 h, additional methyl bromoacetate (0.30 mL) was added. The reaction mixture was stirred for 3.5 h and then the reaction mixture was diluted with H2O (50 mL) and extracted with CH2Cl2 (4×25 mL). The extracts were washed with brine (3×25 mL), dried (Na2SO4) and concentrated. Purification by flash chromatography (silica gel, CH2Cl2/MTBE, 4:1) yielded the title compound (0.77 g, 56%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.10 (s, 1H), 7.73 (s, 1H), 7.43 (s, 2H), 7.30 (d, J=7.5 Hz, 1H), 6.97 (s, 1H), 6.60 (d, J=7.0 Hz, 1H), 5.21 (s, 2H), 3.77 (s, 3H).

Workup

  1. waitAfter 3 h
  2. stirringThe reaction mixture was stirred for 3.5 h
  3. extractionextracted with CH2Cl2 (4×25 mL)
  4. washThe extracts were washed with brine (3×25 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash chromatography (silica gel, CH2Cl2/MTBE, 4:1)

Sources & evidence

ORD record
ord-b9f97bf3578a4af79a7b3a009e41f34b
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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