Methyl chloroformate → HCID 69317586, compound

HRID 2373212Notes

Reaction equation

HRID 2373212 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:23][O:24][CH3:25])=[C:10](/[CH:19]=[CH:20]/[CH2:21][OH:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:36]([O:38][CH3:39])=[O:37]>C(Cl)Cl>[C:36](=[O:37])([O:38][CH3:39])[O:22][CH2:21]/[CH:20]=[CH:19]/[C:10]1[C:11]([C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=2)=[C:6]2[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]2=[N:8][C:9]=1[CH2:23][O:24][CH3:25]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 11702825HCID 11702825, compound

Product 1

HCID 69317586HCID 69317586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of (2E)-3-[1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridinyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-2-propen-1-ol (44 mg) and diisopropylethylamine (20 mg) in DCM (1 ml) was added methyl chloroformate (13.5 mg) and stirred for 2 hours at room temperature. The solvent was dried up and the residue was purified with silica gel column chromatography (CHCl3-MeOH 0-2%). (2E)-3-[1-Ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-2-propen-1-yl methyl carbonate was obtained as a clear oil.

Workup

  1. customThe solvent was dried up
  2. customthe residue was purified with silica gel column chromatography (CHCl3-MeOH 0-2%)

Sources & evidence

ORD record
ord-0fc0cb1308134088924c22384cd7a41d
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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