Hydrochloric Acid → HCID 57731592, compound

HRID 2234690Notes

Reaction equation

HRID 2234690 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=2)[N:11]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH:10]=1.[F:37][C:38]1[C:39]([NH:48][CH:49]2[CH2:54][CH2:53][CH:52]([OH:55])[CH2:51][CH2:50]2)=[C:40]([CH:44]=[C:45](I)[CH:46]=1)[C:41]([OH:43])=[O:42].C(=O)([O-])[O-].[Na+].[Na+].Cl>CC(N(C)C)=O.O>[F:37][C:38]1[C:39]([NH:48][CH:49]2[CH2:54][CH2:53][CH:52]([OH:55])[CH2:51][CH2:50]2)=[C:40]([CH:44]=[C:45]([C:15]2[CH:16]=[C:17]3[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[CH:10][N:11]([S:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)(=[O:28])=[O:29])[C:12]3=[N:13][CH:14]=2)[CH:46]=1)[C:41]([OH:43])=[O:42]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 160390673-(2-Methoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 57731587HCID 57731587, compound

Product 1

HCID 57731592HCID 57731592, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(2-Methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.24 g, 3.27 mmol), 3-Fluoro-2-(4-hydroxy-cyclohexylamino)-5-iodo-benzoic acid (1.65 g, 3.27 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichlormethane adduct (66 mg, 0.08 mmol) in dimethylacetamide (20 mL) and aqueous solution of sodium carbonate (2M, 4.9 mL) was stirred at 100° C. for 14 h. The cooled reaction mixture was poured into 150 mL of water acidified with 6 N hydrochloric acid and filtered. The solids were redissolved in a mixture of dichloromethane and ethanol and filtered again. The filtrate was concentrated and the brown residue was purified by flash silica gel chromatography using a gradient of a solution of 90 parts ethyl acetate, 10 parts methanol, and one part acetic acid and hexanes afforded 1.5 g of a light brown solid (2.38 mmol, 76% yield). MS: m/z 630 [MH+]

Workup

  1. customThe cooled reaction mixture
  2. filtrationfiltered
  3. dissolutionThe solids were redissolved in a mixture of dichloromethane and ethanol
  4. filtrationfiltered again
  5. concentrationThe filtrate was concentrated
  6. customthe brown residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-dc579245034e4c99a14c08ebc03e4917
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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