Tribromoborane-methyl sulfide → HCID 18186390, compound

HRID 1358053Notes

Reaction equation

HRID 1358053 reaction equation
[CH3:1][N:2]([CH3:41])[C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH:16]3[C:25]4[C:20](=[CH:21][C:22]([O:26]CC5C=CC=CC=5)=[CH:23][CH:24]=4)[CH2:19][CH2:18][N:17]3[C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[B-](Br)(Br)(Br)[S+](C)C>ClCCl>[CH3:41][N:2]([CH3:1])[C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH:16]3[C:25]4[C:20](=[CH:21][C:22]([OH:26])=[CH:23][CH:24]=4)[CH2:19][CH2:18][N:17]3[C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4181510Tribromoborane-methyl sulfideHCID 69524407HCID 69524407, compound

Product 1

HCID 18186390HCID 18186390, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-({4-[6-(dimethylamino)(3-pyridyl)]phenyl}mehyl)-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (0.58 g, 1.07 mmol) in anhydrous dichloromethane (10 mL) under nitrogen at room temperature was added 1.0 M solution of boron tribromide-methyl sulfide complex in dichloromethane dropwise. After stirring for 5 hours, the reaction was quenched with ice-water and extracted with ethyl acetate. The extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 30-50% ethyl acetate/hexane) to provide the title compound (0.346 g, 71% yield): 1H NMR (CDCl3) 8.42 (d, 1H), 7.69 (dd, 1H), 7.38 (m, 2H), 7.05 (d, 2H), 6.93 (m, 2H), 6.79 (m, 2H), 6.53-6.67 (m, 4H), 5.09 (br, 1H), 4.76 (t, 1H), 3.58 (m, 1H), 3.48 (m, 1H), 3.17 (m 1H), 3.13 (s, 6H), 2.92 (m, 2H), 2.07 (dt, 1H); ES-MS m/z 454 [M+H]+.

Workup

  1. customthe reaction was quenched with ice-water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was then purified by chromatography (SiO2, 30-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-404cc5b440cc4a2e9fd3c1788e1299f6
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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