Methyl chloroformate → methyl {4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}carbamate

HRID 1727696Notes

Reaction equation

HRID 1727696 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[CH:16][C:9]=23)[C:5]([C:17]2[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=2)=[N:4]1)[CH3:2].Cl[C:25]([O:27][CH3:28])=[O:26]>N1C=CC=CC=1>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[CH:16][C:9]=23)[C:5]([C:17]2[CH:23]=[CH:22][C:20]([NH:21][C:25](=[O:26])[O:27][CH3:28])=[CH:19][CH:18]=2)=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 689998134-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]aniline

Product 1

HCID 58980025methyl {4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}carbamateYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]aniline (0.18 mmol) in pyridine (1.5 mL) was added methyl chloroformate (0.18 mmol). After 3.5 h, the reaction mixture was quenched with methanol and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC provided the title product as a pale yellow powder (40%). ESMS [M+H]+: 362.2

Workup

  1. customthe reaction mixture was quenched with methanol
  2. concentrationconcentrated in vacuo
  3. customPurification of the residue by Gilson reverse phase HPLC

Sources & evidence

ORD record
ord-bc7220340ced42e682c3015d5098aed3
Source dataset
uspto-grants-2009_02
Patent number
US07495102B2

Reaction notes

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