5-(Bromomethyl)-1-methyl-1H-benzotriazole → HCID 67219816, compound

HRID 1445626Notes

Reaction equation

HRID 1445626 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].[CH3:16]CN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.BrC[C:36]1[CH:45]=[CH:44][C:39]2[N:40]([CH3:43])[N:41]=[N:42][C:38]=2[CH:37]=1>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]([CH2:16][C:45]2[CH:36]=[CH:37][C:38]3[N:42]=[N:41][N:40]([CH3:43])[C:39]=3[CH:44]=2)[C:6]=1[CH3:14]

Participants

5

Reactant 3

HCID 27954185-(Bromomethyl)-1-methyl-1H-benzotriazoleHCID 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 67219816HCID 67219816, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester ((0.025 g, 0.122 mmol) in dry DMF (1 ml) under an inert atmosphere of Argon is added dropwise, BEMP (56.6 μl, 0.196 mmol). The mixture is agitated at room temperature for 1 hour before cooling to 0° C. with an ice-bath. A solution of 5-bromomethyl-1-methyl-1H-benzotriazole (0.044 g, 0.196 mmol) in DMF (1 ml) is added to the cooled solution and the resulting mixture is agitated at room temperature for 2 days. The solvent is removed in vacuo and purification of the crude by chromatography on silica eluting with iso-hexane/ethyl acetate (0%-20% ethyl acetate) yields the titled product. (MH+ 350).

Workup

  1. temperaturebefore cooling to 0° C. with an ice-bath
  2. stirringthe resulting mixture is agitated at room temperature for 2 days
  3. customThe solvent is removed in vacuo and purification of the crude by chromatography on silica eluting with iso-hexane/ethyl acetate (0%-20% ethyl acetate)

Sources & evidence

ORD record
ord-4142e9ba9313453182e20849e112de67
Source dataset
uspto-grants-2010_02
Patent number
US07666878B2

Reaction notes

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