Tetrahydrofuran → HCID 67219284, compound

HRID 1254860Notes

Reaction equation

HRID 1254860 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].[O:34]1[CH:38]=[CH:37][C:36]([CH2:39]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:35]1.C1COCC1>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]([CH2:39][C:36]2[CH:37]=[CH:38][O:34][CH:35]=2)[C:24]=1[CH3:32]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 13070594HCID 13070594, compoundHCID 67218699methyl 2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

Product 1

HCID 67219284HCID 67219284, 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 (80 mg, 0.39 mmol) in DMF (1.2 ml). After 30 minutes, a solution of toluene-4-sulfonic acid furan-3-ylmethyl ester in THF (1.4 ml, 0.45 mmol) is added. After 18 hours, the reaction is partitioned between water and 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-furan-3-ylmethyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester; MH+=285.

Workup

  1. waitAfter 18 hours
  2. customthe reaction is partitioned between water and 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-8b9044a58bfe4f8b834b1b07d0bc9b08
Source dataset
uspto-grants-2013_06
Patent number
US08455645B2

Reaction notes

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