Ethyl bromoacetate → Acetic acid, 2-[(3-chloro-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy]-, ethyl ester

HRID 402488Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[C:9]([CH3:11])=[CH:8][C:7](=[O:12])[NH:6][C:5]=2[N:4]([CH3:13])[N:3]=1.CCN(C(C)C)C(C)C.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C>[Cl:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([O:12][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:8][C:9]=2[CH3:11])[N:4]([CH3:13])[N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

3-chloro-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (720 mg, 3.64 mmol) was dissolved in DMF (5 ml) at rt. Then, DIPEA (1.04 g, 8.0 mmol) and ethyl 2-bromoacetate (0.60 ml, 5.5 mmol) were added and the mixture heated at 90° C. After 1 h, the mixture was cooled to rt, the solvent removed under reduced pressure and the residue purified by column chromatography (eluent 70% hexane in EtOAc) to yield 664 mg (64%) of the title compound. [1H-NMR (DMSO-d6, 400 MHz) δ 6.67 (s, 1H), 4.98 (s, 2H) 4.17 (q, 2H), 3.84 (s, 3H), 2.62 (s, 3H), 1.19 (t, 3H); HPLC-MS RtJ=1.13 min; [M+H]+=284.0, 286.0

Workup

temperaturethe mixture was cooled to rt
customthe solvent removed under reduced pressure
customthe residue purified by column chromatography (eluent 70% hexane in EtOAc)

Sources & evidence

ORD record: ord-528e96290ed243698f2ae76795010e27
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742106B2

Reaction notes

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