Potassium Carbonate → (3-{2-[2-(4-Chloro-phenoxy)-ethyl]-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2,3]thiadiazin-4-yl}-5-fluoro-2-methyl-indol-1-yl)-acetic acid tert-butyl ester

HRID 1453767Notes

Reaction equation

HRID 1453767 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([CH3:28])=[C:22]2[C:29]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[S:32](=[O:40])(=[O:39])[NH:31][N:30]=1.Br[CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>CC#N.O.C(Cl)Cl>[C:46]([O:45][C:43](=[O:44])[CH2:42][N:24]1[C:25]2[C:21](=[CH:20][C:19]([F:18])=[CH:27][CH:26]=2)[C:22]([C:29]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[S:32](=[O:39])(=[O:40])[N:31]([CH2:2][CH2:3][O:4][C:5]3[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=3)[N:30]=2)=[C:23]1[CH3:28])([CH3:49])([CH3:48])[CH3:47]

Participants

8

Reactant 4

HCID 11430Potassium Carbonate2×HCID 748541-(2-Bromoethoxy)-4-chlorobenzeneHCID 79177tert-Butyl bromoacetateHCID 1363886124-(5-Fluoro-2-methyl-1H-indol-3-yl)-2H-benzo[e][1,2,3]thiadiazine 1,1-dioxide

Product 1

HCID 67316049(3-{2-[2-(4-Chloro-phenoxy)-ethyl]-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2,3]thiadiazin-4-yl}-5-fluoro-2-methyl-indol-1-yl)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

4-Chlorophenyl 2-bromoethyl ether (16 mg, 67 μmol) and K2CO3 (10 mg, 72 μmol) were added to a solution of 4-(5-fluoro-2-methyl-1H-indol-3-yl)-2H-benzo[e][1,2,3]thiadiazine 1,1-dioxide (20 mg, 61 μmol) in CH3CN (1 mL), and stirred overnight at 80° C. An additional amount of K2CO3 (10 mg, 72 μmol) and tert-butyl bromoacetate (14 μL, 92 μmol) was added, and the reaction mixture stirred an additional 2 h at 80° C. The reaction mixture was diluted with H2O and CH2Cl2, and filtered through an Extrelut column. The Extrelut column was washed with CH2Cl2, and the filtrate was concentrated to afford the sub-title compound, which was carried onto the next step without further purification or characterization.

Workup

  1. stirringthe reaction mixture stirred an additional 2 h at 80° C
  2. filtrationfiltered through an Extrelut column
  3. washThe Extrelut column was washed with CH2Cl2
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-65264a905a6e48448ee3772a1d301385
Source dataset
uspto-grants-2009_01
Patent number
US07476667B2

Reaction notes

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