(Dimethyl sulfide)trihydroboron → HCID 58203957, compound

HRID 1190555Notes

Reaction equation

HRID 1190555 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:23][C:22]3[C:21]4[N:24]=[C:25]([N:28]5[CH2:33][C@H:32]([CH3:34])[N:31]([C:35](=O)[C:36]([F:39])([F:38])[F:37])[C@H:30]([CH3:41])[CH2:29]5)[CH:26]=[CH:27][C:20]=4[O:19][CH2:18][CH2:17][C:16]=3[CH:15]=2)=[N:12][CH:11]=[N:10]1.B.CSC>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:23][C:22]3[C:21]4[N:24]=[C:25]([N:28]5[CH2:33][C@H:32]([CH3:34])[N:31]([CH2:35][C:36]([F:37])([F:38])[F:39])[C@H:30]([CH3:41])[CH2:29]5)[CH:26]=[CH:27][C:20]=4[O:19][CH2:18][CH2:17][C:16]=3[CH:15]=2)=[N:12][CH:11]=[N:10]1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 58203890HCID 58203890, compound

Product 1

HCID 58203957HCID 58203957, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of compound 316 (100 mg, 0.17 mmol) in tetrahydrofuran (5 mL) was added a solution of borane/dimethylsulfane (10 mol/L, 2 mL) dropwise at 0° C. After the addition was completed, the reaction mixture was stirred at that temperature for 30 min and then allowed to warm to 50° C. After stirred for another 1 hour the reaction mixture was quenched by adding 15 mL of methanol and 5 mL of 1 M HCl aqueous solution slowly. The mixture was stirred at room temperature for 2 hours before concentration to the residue. The mixture was treated with dichloromethane and water. The organic layer was concentrated to dryness and the crude was purified by pre-TLC (Hexanes/EtOAc=1:1) to afford 60 mg of 351. (Yield: 61%) 1H NMR (CDCl3, 400 MHz): δ8.02 (s, 1H), 7.51-7.46 (m, 1H), 7.09-6.97 (m, 4H), 6.45 (d, J=8.8 Hz, 1H), 4.18 (t, J=4.8 Hz, 2H), 3.84-3.80 (m, 2H), 3.27 (q, J=9.6 Hz, 2H), 3.07 (t, J=4.8 Hz, 2H), 2.84 (d, J=6.8 Hz, 2H), 2.57-2.51 (m, 2H), 1.22-1.34 (d, J=6.0 Hz, 6H). LC-MS (ESI): m/z=577 [M+H]+

Workup

  1. additionAfter the addition
  2. stirringAfter stirred for another 1 hour the reaction mixture
  3. customwas quenched
  4. additionby adding 15 mL of methanol and 5 mL of 1 M HCl aqueous solution slowly
  5. stirringThe mixture was stirred at room temperature for 2 hours before concentration to the residue
  6. additionThe mixture was treated with dichloromethane and water
  7. concentrationThe organic layer was concentrated to dryness
  8. customthe crude was purified by pre-TLC (Hexanes/EtOAc=1:1)

Sources & evidence

ORD record
ord-e2cacb2a37da4226bfe8b277ecc9b4d2
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

Loading…