Benzyl Bromide → HCID 67219482, compound

HRID 1260597Notes

Reaction equation

HRID 1260597 reaction equation
CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[CH3:19][O:20][C:21](=[O:33])[CH2:22][C:23]1[C:31]2[C:26](=[N:27][CH:28]=[CH:29][CH:30]=2)[NH:25][C:24]=1[CH3:32].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C=O)C>[CH3:19][O:20][C:21](=[O:33])[CH2:22][C:23]1[C:31]2[C:26](=[N:27][CH:28]=[CH:29][CH:30]=2)[N:25]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:24]=1[CH3:32]

Participants

5

Reactant 3

HCID 7498Benzyl 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 67219482HCID 67219482, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

BEMP (182 μL, 0.63 mmol) is added to a stirring solution of (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester prepared as described in U.S. Pat. No. 3,320,268 (80 mg, 0.39 mmol) in DMF (2.4 mL). After 30 minutes, benzyl bromide (75 μL, 0.63 mmol) is added and the reaction stirred for 3 days, before partitioning between water and 1:1 EtOAc/ether. The organic layer is washed with brine then reduced in vacuo. The residue is purified by flash column chromatography (3:1 iso-hexane/EtOAc elution) to furnish (1-benzyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid methyl ester; MH+=295.

Workup

  1. customprepared
  2. custombefore partitioning between water and 1:1 EtOAc/ether
  3. washThe organic layer is washed with brine
  4. customThe residue is purified by flash column chromatography (3:1 iso-hexane/EtOAc elution)

Sources & evidence

ORD record
ord-ad393d38ff7044d08aba250f157202b6
Source dataset
uspto-grants-2013_06
Patent number
US08470848B2

Reaction notes

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