4-(Methylsulfonyl)benzyl Bromide → methyl 2-(2-methyl-1-(4-(methylsulfonyl)benzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

HRID 1260646Notes

Reaction equation

HRID 1260646 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH3:14].CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[CH3:34][S:35]([C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1)(=[O:37])=[O:36]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:42][C:41]2[CH:40]=[CH:39][C:38]([S:35]([CH3:34])(=[O:37])=[O:36])=[CH:45][CH:44]=2)[C:6]=1[CH3:14]

Participants

5

Reactant 3

HCID 27335814-(Methylsulfonyl)benzyl BromideHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 67218699methyl 2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

Product 1

HCID 67219273methyl 2-(2-methyl-1-(4-(methylsulfonyl)benzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester ((6.8 g, 33.5 mmol) in dry DMF (150 ml) under an inert atmosphere of Argon is treated with BEMP (10.5 ml, 36.5 mmol) dropwise, over two minutes. The solution is stirred at room temperature for 1 hour and then a solution of 4-methylsulphonyl benzyl bromide (10.0 g, 40.2 mmol) in DMF (60 ml) is added dropwise over 5 minutes. After stirring at room temperature overnight, the solvent is removed in vacuo and azeotroped with toluene (200 ml). The resulting crude is purified by chromatography on silica eluting with ethyl acetate/iso-hexane (20-100% ethyl acetate) to yield the titled compound as a green oil. (MH+ 373)

Workup

  1. stirringAfter stirring at room temperature overnight
  2. customthe solvent is removed in vacuo
  3. customazeotroped with toluene (200 ml)
  4. customThe resulting crude is purified by chromatography on silica eluting with ethyl acetate/iso-hexane (20-100% ethyl acetate)

Sources & evidence

ORD record
ord-21a29d0d86b547cda7fead283c29b332
Source dataset
uspto-grants-2013_06
Patent number
US08470848B2

Reaction notes

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