Sodium Carbonate → HCID 59362525, compound

HRID 1625445Notes

Reaction equation

HRID 1625445 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=[C:13]3[C:12](I)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:21][C:22]1[CH:23]=[C:24]([CH:46]=[CH:47][C:48]=1[F:49])[CH2:25][N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([NH:34][CH2:35][C:36]2[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=2)=[O:33])[C:27]1=[O:45].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=[C:13]3[C:12]([C:40]3[CH:41]=[C:36]([CH:37]=[CH:38][CH:39]=3)[CH2:35][NH:34][C:32]([C:28]3[C:27](=[O:45])[N:26]([CH2:25][C:24]4[CH:46]=[CH:47][C:48]([F:49])=[C:22]([F:21])[CH:23]=4)[CH:31]=[CH:30][CH:29]=3)=[O:33])=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 242292401-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridineHCID 59362353HCID 59362353, compound

Product 1

HCID 59362525HCID 59362525, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Into a vial was dissolved 1-benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (581 mg, 0.00125 mol) and 3-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-phenylboronic acid (453 mg, 0.00114 mol) and palladium acetate (13 mg, 0.000057 mol; Strem) and triphenylphosphine (32 mg, 0.00012 mol; Aldrich) in acetone (5.4 mL, Acros;). To this was added 2.0 M of sodium carbonate in water (1.8 mL). The vial was flushed under an atmosphere of argon and sealed and was heated at 75 Celsius for 1 hour. The reaction was evaporated then diluted with methylene chloride, washed with water, dried with magnesium sulfate, filtered, and concentrated. The residue was taken up in methylene chloride and purified by silica gel chromatography using hexanes/ethyl acetate as eluent (Rf=0.33 in 1:3 hexanes/ethyl acetate) to yield 663.8 mg (85%) of product. MS m/z=689.09 M+H.

Workup

  1. customThe vial was flushed under an atmosphere of argon
  2. customsealed
  3. customThe reaction was evaporated
  4. additionthen diluted with methylene chloride
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f9206798bf2f4424b2a7930a856aa84b
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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