(Dimethyl sulfide)trihydroboron → HCID 70011993, compound

HRID 1859636Notes

Reaction equation

HRID 1859636 reaction equation
B.CSC.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:13][C:14]([CH:23]3[CH2:28][CH2:27][N:26]([C:29]([C:31]4(O)[CH2:33][CH2:32]4)=[O:30])[CH2:25][CH2:24]3)=[CH:15][C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:8][CH:7]=1>C1COCC1>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:13][C:14]([CH:23]3[CH2:28][CH2:27][N:26]([CH:29]([OH:30])[CH:31]4[CH2:33][CH2:32]4)[CH2:25][CH2:24]3)=[CH:15][C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 70011815HCID 70011815, compound

Product 1

HCID 70011993HCID 70011993, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulfide complex (1.68 mL, 2.0 M solution in THF) was added drop wise to stirred solution of the product of Step 1 (224 mg) in dry THF (5 mL) under nitrogen. After 16 h at room temperature, the solution was cooled, and excess borane was quenched with methanol. The solvent was evaporated to dryness, and the residue was dissolved in THF (5 mL). 2-(Dimethylamino)ethanol (0.67 mL) was added, and the reaction mixture was heated under reflux for 3 h, cooled, and evaporated to dryness. The residue was purified by preparative TLC (CH2Cl2—MeOH, 90:10) to give the title compound (50 mg). NMR (CD3OD): 0.54-0.59 (m, 2H, cyclopropyl),0.75-0.77 (m, 2H, cyclopropyl),1.85, 2.02, 2.32, 2.61 (4 m, 8H, piperidinyl),2.64-2.69 (m, 1H, CH),3.26-3.29 (d, 2H, CH2),6.20 (s, 1H, H-4),7.08-7.11 (m, 2H, H-2 & H-6 of 4-F-phenyl),7.24-7.26 (m, 2H, H-2 & H-6 of pyridinyl),7.33-7.37 (m, 2H, H-3 & H-5 of 4-F-phenyl),8.24-8.26 (m, 2H, H-3 & H-5 of pyridinyl)

Workup

  1. temperaturethe solution was cooled
  2. customexcess borane was quenched with methanol
  3. customThe solvent was evaporated to dryness
  4. dissolutionthe residue was dissolved in THF (5 mL)
  5. addition2-(Dimethylamino)ethanol (0.67 mL) was added
  6. temperaturethe reaction mixture was heated
  7. temperatureunder reflux for 3 h
  8. temperaturecooled
  9. customevaporated to dryness
  10. customThe residue was purified by preparative TLC (CH2Cl2—MeOH, 90:10)

Sources & evidence

ORD record
ord-5c021474611c4f929db473220310b99f
Source dataset
uspto-grants-2003_03
Patent number
US06528531B1

Reaction notes

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