Cesium carbonate → HCID 66665908, compound

HRID 2276517Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:13][CH2:12][CH2:11][CH2:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CN1C(=O)CCC1>[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:13]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:12][CH2:11][CH2:10]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of 6,7-diphenyl-1,2,3,4-tetrahydro-[1,8]naphthyridine (Intermediate B) (200 mg, 0.698 mmol) in dry NMP (1 ml) under N2 was treated with cesium carbonate (910 mg, 2.79 mmol) and ethyl 7-bromoheptanoate (0.544 ml, 2.79 mmol). The reaction mixture was stirred at 120° C. for 1 h and a further 3 h at 140° C. After cooling to room temperature, the mixture was partitioned between EtOAc and water. The organic portion was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 4:1 iso-hexane/EtOAc afforded a pink oil residue.

Workup

temperatureAfter cooling to room temperature
customthe mixture was partitioned between EtOAc and water
washThe organic portion was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the crude product by chromatography on silica eluting with 4:1 iso-hexane/EtOAc
customafforded a pink oil residue

Sources & evidence

ORD record: ord-f365bb1ad64e4ecfa245f671ba8c93fb
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09132127B2

Reaction notes

Loading…