Dichloromethane → HCID 57595703, compound

HRID 1964989Notes

Reaction equation

HRID 1964989 reaction equation
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[C:11]2[C:10]([C:22](=[O:31])[C:23]2[CH:28]=[CH:27][C:26]([O:29]C)=[CH:25][CH:24]=2)=[CH:9]1)=O)(C)(C)C.C(Cl)Cl.B(Br)(Br)Br>CO>[OH:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]([C:10]2[C:11]3[C:12](=[N:13][CH:14]=[C:15]([C:17]4[S:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=3)[NH:8][CH:9]=2)=[O:31])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 58087616HCID 58087616, compound

Product 1

HCID 57595703HCID 57595703, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-Methoxy-benzoyl)-5-thiophen-2-yl-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (118, 100.0 mg, 0.23 mmol) and methylene chloride (15.0 mL) were combined under an atmosphere of nitrogen. Boron tribromide (1.0 M in methylene chloride, 3.0 mL) was added. The reaction was stirred at room temperature overnight. Methanol (2.0 mL) was added into the the reaction mixture. The reaction was concentrated to remove solvents. The residue was extracted with water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified with silica gel chromatography. The product was washed with methanol to provide compound (P-0024, 25.0 mg, 34%). MS(ESI) [M+H+]+=321.

Workup

  1. concentrationThe reaction was concentrated
  2. customto remove solvents
  3. extractionThe residue was extracted with water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified with silica gel chromatography
  8. washThe product was washed with methanol
  9. customto provide compound (P-0024, 25.0 mg, 34%)

Sources & evidence

ORD record
ord-22a66e9502c84d7f9a401973d8b05848
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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