Potassium Carbonate → HCID 86728234, compound

HRID 1776819Notes

Reaction equation

Cl[CH2:2]I.C([O-])([O-])=O.[K+].[K+].[Cl:10][C:11]1[N:16]=[C:15]([C:17]2[NH:25][C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)[C:14]([OH:26])=[CH:13][CH:12]=1>CN(C=O)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[O:26][CH2:2][N:25]3[C:20]4[N:21]=[CH:22][CH:23]=[CH:24][C:19]=4[CH:18]=[C:17]3[C:15]=2[N:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of chloroiodomethane (2.01 g, 11.40 mmol), K2CO3 (338 mg, 2.44 mmol) in DMF (15 mL), 6-chloro-2-(1H-pyrrolo[2,3-b]pyridin-2-yl)pyridin-3-ol (200 mg, 0.81 mmol) in DMF (5 mL) was added dropwise at 100° C. under N2 protection. After stirred at 100° C. for 2 hours, the reaction mixture was concentrated in vacuo, suspended in water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified using prep-TLC (petroleum ether:EtOAc=8:1) to provide the product of 2-chloro-6H-pyrido[2,3-e]pyrido[3′,2′:4,5]pyrrolo[1,2-c][1,3]oxazine (20 mg, yield: 9%). 1H-NMR (CDCl3, 400 MHz) δ 8.35 (dd, J=4.8 Hz, 1.6 Hz, 1H), 7.99 (dd, J=8.0 Hz, 1.6 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.21 (d, J=8.4 Hz, 1H), 7.16 (s, 1H), 7.13 (dd, J=8.0 Hz, 4.8 Hz, 1H), 6.14 (s, 2H). MS (M+H)+: 258/260.

Workup

additionwas added dropwise at 100° C. under N2 protection
concentrationthe reaction mixture was concentrated in vacuo
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe crude product was purified

Sources & evidence

ORD record: ord-8c130d1e72cc478997169ae0f157c5f3
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265773B2

Reaction notes

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