Water → 1-(4-Chloro-[1,3,5]-triazin-2-yl)-5-methanesulfonyl-2,3-dihydro-1H-indole

HRID 448575

Reaction equation

[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH2:9][CH2:8]2)(=[O:4])=[O:3].[Cl:14][C:15]1[N:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:14][C:15]1[N:20]=[CH:19][N:18]=[C:17]([N:10]2[C:11]3[C:7](=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:13][CH:12]=3)[CH2:8][CH2:9]2)[N:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5-Methanesulfonyl-2,3-dihydro-1H-indole (79 mg, 0.4 mmol) was dissolved in dioxane (2 mL). 2,4-Dichloro-[1,3,5]-triazine (60 mg, 1 eq), palladium acetate (11 mg, 5% molar), (+/−)binap (15 mg, 8% molar) and cesium carbonate (131 mg, 1 eq) were added and the reaction mixture was heated at 100° C. for 4 h. The mixture was cooled to room temperature and water was added. The mixture was filtered through celite and washed three times with dioxane. The collected filtrate was evaporated to dryness to give 11a (104 mg) which was used for the next step without further purification.

Workup

temperatureThe mixture was cooled to room temperature
filtrationThe mixture was filtered through celite
washwashed three times with dioxane
customThe collected filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-c6be3730c18143329c854589768305da
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481731B2

Linked notes

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