Triphenylphosphine → 1-(3-Bromo-1-methylpropyl)-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][S:9]1(=[O:18])=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:38][CH2:39][CH2:40][CH:41](O)[CH3:42].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:38][CH2:39][CH2:40][CH:41]([N:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[S:9]1(=[O:18])=[O:17])[CH3:42]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
1-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (general procedure 10.2 g, 0.8 mmol) was dissolved in tetrahydrofuran (10 mL) and triphenylphosphine (0.54 g, 0.9 mmol) was added followed by 4-bromobutan-2-ol (0.14 g, 0.9 mmol) and diisopropyl azodicarboxylate (0.18 g, 0.9 mmol). The mixture was stirred for 18 hours at 23° C. The mixture was concentrated and purified via Isco chromatography (Redisep, silica, gradient 0-50% ethyl acetate in hexane) to afford 0.22 g of 1-(3-bromo-1-methylpropyl)-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide.
Workup
- concentrationThe mixture was concentrated
- custompurified via Isco chromatography (Redisep, silica, gradient 0-50% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-e6f26e73ec794086b79cdfa179a2f8da
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601722B2
Reaction notes
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