Sodium Carbonate → HCID 67203834, compound

HRID 1615389Notes

Reaction equation

[C:1]([O:7][CH2:8][N:9]1[C:13]2[N:14]=[CH:15][N:16]=[C:17]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([N+:33]([O-])=O)[CH:28]=5)[CH:25]=4)[CH:20]=[CH:19]3)[C:12]=2[CH:11]=[CH:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].O.O.[Sn](Cl)Cl.O.N.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C(OCC)(=O)C>[C:1]([O:7][CH2:8][N:9]1[C:13]2[N:14]=[CH:15][N:16]=[C:17]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([NH2:33])[CH:28]=5)[CH:25]=4)[CH:20]=[CH:19]3)[C:12]=2[CH:11]=[CH:10]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

(4-(6-(3-Nitrophenyl)-1H-indol-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate (166 mg, 0.35 mmol) was dissolved in ethanol (5 mL). After adding tin(II) chloride dihydrate (SnCl2.2H2O; 80 mg, 1.75 mmol), the reaction mixture was stirred at 80° C. for 1.5 hours. After cooling to room temperature and alkalinizing the reaction mixture to pH 8 with ammonia water, ethyl acetate and sodium carbonate were added. The mixture solution was filtered through a diatomite pad and the filtrate was concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, DCM:MeOH=20:1) yielded (4-(6-(3-aminophenyl)-1H-indol-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate (120 mg, 0.27 mmol) as ivory solid.

Workup

temperatureAfter cooling to room temperature
additionwere added
filtrationThe mixture solution was filtered through a diatomite pad
concentrationthe filtrate was concentrated under reduced pressure
customPurification of the residue by column chromatography (silica gel, DCM:MeOH=20:1)

Sources & evidence

ORD record: ord-008b0bb7f8af438996f44b3024c41be3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765749B2

Reaction notes

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