Sodium Carbonate → HCID 57537527, compound

HRID 1693725Notes

Reaction equation

HRID 1693725 reaction equation
[NH2:1][C:2]1[N:12]=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].Br[C:23]1[C:24]([Cl:49])=[C:25]2[C:31]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=3[O:39][CH3:40])=[CH:30][N:29]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:26]2=[N:27][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[NH2:1][C:2]1[N:12]=[CH:11][C:10]([C:23]2[C:24]([Cl:49])=[C:25]3[C:31]([C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=4[O:39][CH3:40])=[CH:30][N:29]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:26]3=[N:27][CH:28]=2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:7])[CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 575375112-Amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinecarboxamideHCID 57537608HCID 57537608, compound

Product 1

HCID 57537527HCID 57537527, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 20 mL Personal Chemistry microwave reaction vial were added 2-Amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinamide (1.55 g, 5.35 mmol), 5-Bromo-4-chloro-3-(4-chloro-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (1.58 g, (3.15 mmol), bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct (129 mg, 0.158 mmol), sodium carbonate solution (3.15 mL, 6.30 mmol, 2.0 M solution in water) and N,N-dimethylformamide (15 mL). The vial was purged with nitrogen, sealed, and irradiated in a Personal Chemistry Optimizer at 120° C. for 30 minutes. The mixture was concentrated in vacuo. The crude was taken up in dichloromethane (150 mL) and washed with aqueous saturated sodium carbonate solution (1×150 mL) and brine (1×150 mL). The organ phase was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 2-Amino-5-[4-chloro-3-(4-chloro-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide (1.02 g, 1.74 mmol, 55% yield). 1H-NMR [500 MHz, d6-DMSO] δ: 8.26 (s, 1H), 8.06 (d, 1H), 7.72 (s, 1H), 7.48 (d, 1H), 7.26 (d, 1H), 7.11 (d, 1H), 7.03 (dd, 1H), 6.18 (s, 2H), 5.66 (s, 2H), 3.71 (s, 3H), 3.59 (t, 2H), 2.94 (s, 6H), 0.85 (s, 2H), −0.08 (s, 8H); MS [MH+] m/z: 486

Workup

  1. customInto a 20 mL Personal Chemistry microwave reaction
  2. customThe vial was purged with nitrogen
  3. customsealed
  4. customirradiated in a Personal Chemistry Optimizer at 120° C. for 30 minutes
  5. concentrationThe mixture was concentrated in vacuo
  6. washwashed with aqueous saturated sodium carbonate solution (1×150 mL) and brine (1×150 mL)
  7. dry with materialThe organ phase was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-906cbe096fa24053a6bde65b71b18000
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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