Potassium Carbonate → HCID 22048412, compound

HRID 1833196Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[C:12]([C:18](=[O:28])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH3:27])[CH:20]=1)=[N:11][CH:10]=[C:9]2[CH:29]=[O:30].C(=O)([O-])[O-].[K+].[K+].[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>CN(C)C=O.C(OCC)(=O)C.O>[N:37]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][C:15]=2[O:16][CH3:17])[C:12]([C:18](=[O:28])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][CH3:27])[CH:20]=2)=[N:11][CH:10]=[C:9]3[CH:29]=[O:30])[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution 6-(3-bromo-propoxy)-1-(3-ethoxy-benzoyl)-7-methoxy-isoquinoline-4-carbaldehyde (62 g, 0.13 mmol) in N,N-dimethylformamide (2 mL) was added potassium carbonate (181 mg, 1.30 mmol) and pyrrolidine (0.032 mL, 0.66 mmol) at room temperature. The reaction mixture was heated 85° C. for 2 hrs. The mixture was diluted with ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (3×30 mL). The combined extracts were washed with saturated aqueous sodium chloride (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to afford product 6-(3-pyrrolidin-1-yl-propoxy)-7-methoxy-1-(3-ethoxy-benzoyl)-isoquinoline-4-carbaldehyde as a colorless oil (63 mg, 99% yield).

Workup

extractionThe aqueous phase was extracted with ethyl acetate (3×30 mL)
washThe combined extracts were washed with saturated aqueous sodium chloride (50 mL)
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a0acfbfaec5944afa1fbfc3a2e4d7583
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067529B2

Reaction notes

Loading…