4-Methoxybenzene-1-sulfonyl fluoride → 5-Fluoro-6-(4-methoxy-benzenesulfonyl)-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indole

HRID 1475330Notes

Reaction equation

HRID 1475330 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:22])([CH3:21])[CH2:7][N:8]2[Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])=[CH:4][C:3]=1[F:23].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](F)(=[O:34])=[O:33])=[CH:28][CH:27]=1>>[F:23][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[S:32]([C:29]1[CH:28]=[CH:27][C:26]([O:25][CH3:24])=[CH:31][CH:30]=1)(=[O:34])=[O:33])[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH2:7][C:6]2([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 124097114-Methoxybenzene-1-sulfonyl fluorideHCID 867239466-Bromo-5-fluoro-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indole

Product 1

HCID 867239505-Fluoro-6-(4-methoxy-benzenesulfonyl)-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indoleYield 54.9%

Procedure

The title compound was prepared starting from 6-bromo-5-fluoro-3,3-dimethyl-1-triisopropylsilanyl-2,3-dihydro-1H-indole (400 mg, 1.0 mmol) and 4-methoxy-benzenesulfonyl fluoride (190 mg, 1.0 mmol) following similar methods to those Preparation 77 to give the title compound (270 mg) as a yellow oil. 1H NMR (CDCl3): 7.92 (2H, dd), 7.20 (1H, d), 7.01-6.94 (2H, m), 6.67 (1H, d), 3.87 (3H, s), 3.49 (2H, s), 1.56-1.43 (3H, m), 1.25-1.21 (6H, m), 1.17 (18H, d).

Workup

  1. customThe title compound was prepared
  2. customto those Preparation 77

Sources & evidence

ORD record
ord-c5f92b45542e4829ae4fc4802ed13582
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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