Trimethyl phosphite → 4-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 1785585Notes

Reaction equation

HRID 1785585 reaction equation
O(C1C=C([Mg]Br)C=CC=1)[CH3:2].[C:11]([Cu])#[N:12].P(OC)(OC)OC.C(OC([N:28]1[C:32]2=NC=C(C3C=CSC=3)C=[C:31]2[C:30]([CH2:42][Cl:43])=[CH:29]1)=O)(C)(C)C>O1CCCC1.O>[Cl:43][C:42]1[CH:2]=[CH:11][N:12]=[C:29]2[C:30]=1[CH:31]=[CH:32][NH:28]2

Participants

7

Reactant 4

HCID 8472Trimethyl phosphiteHCID 57595601HCID 57595601, compoundHCID 178418546HCID 178418546, compoundHCID 178490745HCID 178490745, compound

Product 1

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-20 °C

Procedure

Into a round bottom flask was added 1.0 M of 3-methoxylphenyl magnesium bromide in Tetrahydrofuran (1.0 mL) and Tetrahydrofuran (5.0 mL, 0.062 mol) under an atmosphere of Nitrogen. The reaction mixture was cooled to −20 Celsius, followed by addition of 0.7 M of CuCN.2LiCl in Tetrahydrofuran (1 mL). After 10 minutes, Trimethyl Phosphite (120 mg, 0.0010 mol) was added to the reaction mixture. To the reaction mixture, was added compound 18 (60.0 mg, 0.000172 mol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water, extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified with biotage to give product 6 (M25 mg).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified with biotage

Sources & evidence

ORD record
ord-76fe9d6c366748d9a9430ed67f67ea7f
Source dataset
uspto-grants-2009_03
Patent number
US07504509B2

Reaction notes

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