Dimethylformamide → HCID 9866320, compound

HRID 1823319Notes

Reaction equation

HRID 1823319 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:27][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]4)(=O)=O)=CC=1.[NH:28]1[CH2:33][CH:32]=[C:31]([C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[NH:36][CH:35]=2)[CH2:30][CH2:29]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>C1COCC1.O>[NH:36]1[C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:34]([C:31]2[CH2:32][CH2:33][N:28]([CH2:12][C@@H:13]3[O:27][C:17]4=[C:18]5[C:23](=[CH:24][CH:25]=[C:16]4[O:15][CH2:14]3)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]5)[CH2:29][CH:30]=2)=[CH:35]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 11280604(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-ylmethyl 4-methylbenzenesulfonate

Product 1

HCID 9866320HCID 9866320, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-methylbenzenesulfonate (0.192 g, 0.499 mmol), 3-(1,2,3,6-tetrahydropyridin4-yl)-1H-indole (0.119 g, 0.601 mmol) and K2CO3 (0.104 g, 0.753 mmol) in (1:1) THF:DMF (1.4 mL) was heated to 80–83° C. for 10 h. After this time, H2O (3 mL) was added and the suspension was filtered. The filtered solid was washed with CH3OH (2×3 mL), Et2O (2×5 mL) and air-dried to give 0.148 g (72%) of the title compound as a tan solid.

Workup

  1. filtrationthe suspension was filtered
  2. washThe filtered solid was washed with CH3OH (2×3 mL), Et2O (2×5 mL)
  3. customair-dried

Sources & evidence

ORD record
ord-18df0459e5514356b9319b299d27759f
Source dataset
uspto-grants-2006_05
Patent number
US07038052B2

Reaction notes

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