Methanol → HCID 9866320, compound

HRID 2116758Notes

Reaction equation

HRID 2116758 reaction equation
BrC1C=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(N(C(C)C)CC)(C)C.CO>CS(C)=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

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleHCID 20624762[(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl4-bromobenzenesulfonate

Product 1

HCID 9866320HCID 9866320, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (2.0 g, 4.44 mmol), 3-(1,2,3,6-tetrahydropyridin4-yl)-1H -indole (1.01 g, 5.09 mmol) and diisopropylethyl amine (0.86 g, 6.65 mmol) in DMSO (10 mL) was heated to 80-83° C. After 10 h, the reaction mixture was cooled to 65-70° C. before CH3OH (3 mL) was added. The resulted suspension was cooled to room temperature, filtered, washed with CH3OH and dried in a vacuum oven to give 1.3 g (71%) of the title compound as a yellow solid.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. washwashed with CH3OH
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-be7e80dbeb334149b6474fedbeea8a24
Source dataset
uspto-grants-2008_10
Patent number
US07439364B2

Reaction notes

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