4-(Bromomethyl)-1,2-dichlorobenzene → [1-(3,4-dichloro-benzyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]acetic acid methyl ester

HRID 1254867Notes

Reaction equation

HRID 1254867 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[Cl:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[Cl:42])[CH2:37]Br>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:37][C:36]2[CH:39]=[CH:40][C:41]([Cl:42])=[C:34]([Cl:33])[CH:35]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 25067325Methyl 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

Product 1

HCID 67219084[1-(3,4-dichloro-benzyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice cold solution of (1H-pyrrolo[2,3-b]pyridine-3-yl)-acetic acid methyl ester (50 mg, 0.26 mmol) in DMF (1 mL), is added BEMP (0.122 mL, 0.42 mmol). The reaction mixture is stirred at ambient temperature for 40 minutes, then 3,4-dichlorobenzyl bromide (0.101 g, 0.42 mmol) is added and the reaction mixture is stirred for 16 hours at ambient temperature. The reaction mixture is poured into ice cold water (40 mL) and extracted with EtOAc, washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude product is purified by column chromatography on silica gel using a pre-packed Isolute™ silica column (2 g) eluting with 1:20 EtOAc/iso-hexane, furnishing [1-(3,4-dichloro-benzyl)-1H-pyrrolo[2,3-b]pyridine-3-yl]-acetic acid methyl ester; MH+=349.

Workup

  1. stirringthe reaction mixture is stirred for 16 hours at ambient temperature
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude product is purified by column chromatography on silica gel using a pre-packed Isolute™ silica column (2 g)
  8. washeluting with 1:20 EtOAc/iso-hexane

Sources & evidence

ORD record
ord-2adea36861374e07bde3b8ce279269d1
Source dataset
uspto-grants-2013_06
Patent number
US08455645B2

Reaction notes

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