2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1H-Pyrrolo[2,3-B]pyridine-5-methanol, 1-[(1,1-dimethylethyl)dimethylsilyl]-

HRID 1994194Notes

Reaction equation

HRID 1994194 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[C:15]([Si:19]([CH3:32])([CH3:31])[N:20]1[C:24]2=[N:25][CH:26]=[C:27]([CH2:29][OH:30])[CH:28]=[C:23]2[CH2:22][CH2:21]1)([CH3:18])([CH3:17])[CH3:16]>C(Cl)Cl.P([O-])([O-])([O-])=O>[C:15]([Si:19]([CH3:32])([CH3:31])[N:20]1[C:24]2=[N:25][CH:26]=[C:27]([CH2:29][OH:30])[CH:28]=[C:23]2[CH:22]=[CH:21]1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 58730943[1-(tert-Butyl-dimethyl-silanyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-5-yl]-methanol

Product 1

HCID 497589901H-Pyrrolo[2,3-B]pyridine-5-methanol, 1-[(1,1-dimethylethyl)dimethylsilyl]-Yield 31%

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 6344DichloromethaneSolvent

Procedure

DDQ (53 mg, 0.23 mmol) was added in three equal portions to a stirred solution of alcohol 14 (54 mg, 0.20 mmol) in a mixture of CH2Cl2 (15 mL) and 0.2 M pH 7 phosphate buffer (0.15 mL). When TLC analysis showed complete consumption of the starting material, the mixture was diluted with saturated aqueous NaHCO3 (16 mL) and stirred vigorously for 1 h. Then the mixture was extracted with AcOEt (2×). The combined organic extracts were washed with saturated brine (1×), dried (MgSO4) and concentrated. The residue was purified by PTLC with benzene as eluent to afford alcohol 15 (16 mg, 31%). 1H NMR (400 MHz; CDCl3) δ 0.63 (s, 6H), 0.93 (s, 9H), 4.77 (s, 2H), 6.52 (d, J=3.5 Hz, 1H), 7.26 (d, J=3.5 Hz, 1H), 7.89 (d, J=2.0 Hz, 1H), 8.28 (d, J=2.0 Hz, 1H).

Workup

  1. customconsumption of the starting material
  2. additionthe mixture was diluted with saturated aqueous NaHCO3 (16 mL)
  3. extractionThen the mixture was extracted with AcOEt (2×)
  4. washThe combined organic extracts were washed with saturated brine (1×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by PTLC with benzene as eluent

Sources & evidence

ORD record
ord-0c20570553674e83b311eedc32e42cba
Source dataset
uspto-grants-2010_01
Patent number
US07652137B2

Reaction notes

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