Triphenylphosphine → 3-(2-bromoethyl)-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

HRID 2237489Notes

Reaction equation

HRID 2237489 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][NH:10][S:9]1(=[O:19])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:39][CH:40](O)[CH3:41].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:39][CH2:40][CH2:41][N:10]1[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[S:9]1(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 14202443Ethanol, 1-bromo-HCID 685811711-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

Product 1

HCID 685822933-(2-bromoethyl)-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxideYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.46 g, 1.7 mmol) in tetrahydrofuran (20 mL) was cool to 0° C. and treated with triphenylphosphine (0.65 g, 2.5 mmol), bromoethanol (0.25 mL, 3.5 mmol) and diisopropyl azodicarboxylate (0.5 mL, 2.6 mmol). After the final addition, the reaction mixture was warmed to room temperature for 2 h, evaporated to a brown oil. The crude product residue was purified by flash chromatography (SiO2, 3-50% ethyl acetate/heptane) to afford 3-(2-bromoethyl)-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.44 g, 63%) as a white solid:

Workup

  1. additionAfter the final addition
  2. customevaporated to a brown oil
  3. customThe crude product residue was purified by flash chromatography (SiO2, 3-50% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-f49ace44da1142ada44b4a31993ef303
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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