Toluene → HCID 57985925, compound

HRID 1869189Notes

Reaction equation

HRID 1869189 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[CH:11][C:4]=12.[CH:12]([Mg]Cl)(C)[CH3:13].CC[C:19]1(CC)[C:25](=[O:26])[O:24][CH:23]([C:27]2C=CC=CC=2)[O:22][C:20]1=[O:21].[C:35]1([CH3:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH2:23]([O:24][C:25](=[O:26])[CH:19]([CH:41]([C:11]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[NH:9][CH:10]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:20]([O:22][CH2:12][CH3:13])=[O:21])[CH3:27]

Participants

5

Reactant 4

HCID 1140TolueneHCID 112405674-Methoxy-1H-pyrrolo[2,3-b]pyridineHCID 54498698HCID 54498698, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 57985925HCID 57985925, compound

Procedure

To a RT suspension of 4-methoxy-1H-pyrrolo[2,3-b]pyridine (prepared as described in WO03/082289, 1.0 g, 6.75 mmol) in toluene (30 ml) at RT was added isopropyl magnesium chloride(1.5 M in THF, 4.95 ml, 7.43 mmol) dropwise. The resulting mixture was stirred at RT for 30 min and neat diethyl benzylidene malonate (1.82 ml, 8.10 mmol) was added dropwise. The reaction was stirred for 1 h then quenched by addition of a saturated solution of NH4Cl and diluted with H2O and EtOAc. The resulting white solid precipitate was filtered and dried affording 2-[(4-Methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-phenyl-methyl]-malonic acid diethyl ester (2.13 g). An additional 130 mg was isolated from the mother liquors, giving 85% combined yield.

Workup

  1. stirringThe reaction was stirred for 1 h
  2. customthen quenched by addition of a saturated solution of NH4Cl
  3. additiondiluted with H2O and EtOAc
  4. filtrationThe resulting white solid precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-01058e6aeb39487eb57af16c98825152
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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