Sodium Carbonate → HCID 57537513, compound

HRID 1693722Notes

Reaction equation

HRID 1693722 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([OH:14])[C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:5]=[N:6][CH:7]=1.C([O-])(=O)C.[K+].Br[C:21]1[C:22]([Cl:46])=[C:23]2[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])=[CH:28][N:27]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:24]2=[N:25][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>CC(N(C)C)=O>[Cl:46][C:22]1[C:21]([C:2]2[CH:3]=[C:4]([CH:8]([OH:14])[C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH:5]=[N:6][CH:7]=2)=[CH:26][N:25]=[C:24]2[N:27]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:43])([CH3:45])[CH3:44])[CH:28]=[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])[C:23]=12

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 517044Potassium AcetateHCID 57537472HCID 57537472, compoundHCID 57537619HCID 57537619, compound

Product 1

HCID 57537513HCID 57537513, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(5-Bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide (400 mg, 1.54 mmol), bis(pinacol)diborane (431 mg, 1.7 mmol), potassium acetate (454 mg, 4.6 mmol), and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (25 mg, 0.03 mmol) in dimethylacetamide (2 mL) was stirred under nitrogen at 120° C. for 12 h. 5-Bromo-3-(2-methoxy-phenyl)-4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (491 mg, 1.05 mmol), sodium carbonate solution (2M in water, 2.3 mL, 4.6 mmol), dimethylacetamide (2 mL) and additional 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (30 mg, 0.035 mmol) was added and the mixture was stirred for an additional 2 h at 120° C. Sodium sulfate was added to the crude reaction mixture and the solids were filtered over Celite. The solids were rinsed with ethyl acetate and acetonitrile and the combined filtrate was concentrated. The resulting oil was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 2-{5-[4-Chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-2-hydroxy-N,N-dimethyl-acetamide (202 mg, 0.35 mmol, 34% yield; and 2-{5-[4-Chloro-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-N,N-dimethyl-acetamide.

Workup

  1. stirringthe mixture was stirred for an additional 2 h at 120° C
  2. customreaction mixture
  3. filtrationthe solids were filtered over Celite
  4. washThe solids were rinsed with ethyl acetate and acetonitrile
  5. concentrationthe combined filtrate was concentrated
  6. customThe resulting oil was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-a06d0c937721464787117acfaa02b2dd
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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