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

HRID 1180827Notes

Reaction equation

HRID 1180827 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-ad84c885fd1040c0a795a8ba3291b449
Source dataset
uspto-grants-2007_10
Patent number
US07282588B2

Reaction notes

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