Potassium Carbonate → HCID 71284744, compound

HRID 1481759Notes

Reaction equation

[CH2:1]([O:8][C:9]1[N:18]=[C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[C:23](Cl)=[C:22]3[C:30]#[N:31])[C:16]([CH2:32][CH3:33])=[C:15]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:48]1[CH2:52][CH2:51][CH2:50][CH2:49]1>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:18]=[C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[C:23]([N:48]2[CH2:52][CH2:51][CH2:50][CH2:49]2)=[C:22]3[C:30]#[N:31])[C:16]([CH2:32][CH3:33])=[C:15]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 2,4-bis(benzyloxy)-6-(2-chloro-3-cyano-1-methyl-1H-indol-5-yl)-5-ethylnicotinate (143 mg, 0.25 mmol) in DMF (2 mL) was added potassium carbonate (70 mg, 0.50 mmol, 2.0 eq) followed by pyrrolidine (0.05 mL, 0.61 mmol, 2.4 eq) at room temperature. The reaction was heated to 60° C. and the progress was monitored by LC-MS. Upon completion, the reaction was quenched with water then extracted with EtOAc (3×25 mL). The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography (0-10% EtOAc in 1/1 CH2Cl2/hexanes) to afford the title compound (134 mg, 89%).

Workup

customUpon completion, the reaction was quenched with water
extractionthen extracted with EtOAc (3×25 mL)
customThe solvent was removed under reduced pressure
customthe crude product was purified by flash column chromatography (0-10% EtOAc in 1/1 CH2Cl2/hexanes)

Sources & evidence

ORD record: ord-252431c3ae7d4dfe8ef38e136c03c2e6
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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