Benzyl Bromide → [3-(2-Benzyl-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 1819629Notes

Reaction equation

[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[F:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH3:25])=[C:19]2[C:26]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[S:29](=[O:37])(=[O:36])[NH:28][N:27]=1.Br[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41]>CC#N.O.C(Cl)Cl>[C:43]([O:42][C:40](=[O:41])[CH2:39][N:21]1[C:22]2[C:18](=[CH:17][C:16]([F:15])=[CH:24][CH:23]=2)[C:19]([C:26]2[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[S:29](=[O:36])(=[O:37])[N:28]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:27]=2)=[C:20]1[CH3:25])([CH3:46])([CH3:45])[CH3:44]

Participants

Conditions

Temperature: 80 °C

Procedure

Benzyl bromide (10 μL, 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

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

Sources & evidence

ORD record: ord-6201f4523176445c94bdb49b5a2e199b
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601749B2

Reaction notes

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