Diethyl Ether → HCID 67219019, compound

HRID 1754472Notes

Reaction equation

HRID 1754472 reaction equation
CCN(P1(N(C)CCCN1C)=[N:7][C:8](C)([CH3:10])[CH3:9])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](OCC)C.[CH3:39][N:40]([CH:42]=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:42]2[N:40]([CH3:39])[N:7]=[C:8]([CH3:10])[CH:9]=2)[C:24]=1[CH3:32]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 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 67219019HCID 67219019, compound

Procedure

BEMP (137 μL, 0.47 mmol) is added to a solution of (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (60 mg, 0.29 mmol) in DMF (0.8 mL). After 35 minutes, the diethyl ether layer from Step 71a (1.8 mL) is added. After 3 days, the reaction is partitioned between water and 1:1 EtOAc/ether. The organic layer is washed with brine then evaporated. The residue is purified by flash column chromatography (49:1 EtOAc/MeOH elution) to furnish [1-(2,5-dimethyl-2H-pyrazol-3-ylmethyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester; MH+=313.

Workup

  1. waitAfter 3 days
  2. customthe reaction is partitioned between water and 1:1 EtOAc/ether
  3. washThe organic layer is washed with brine
  4. customthen evaporated
  5. customThe residue is purified by flash column chromatography (49:1 EtOAc/MeOH elution)

Sources & evidence

ORD record
ord-d505abde21334f3b9f52e5cd0b063a2e
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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