(Dimethyl sulfide)trihydroboron → HCID 86712760, compound

HRID 1754550Notes

Reaction equation

HRID 1754550 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1([CH2:18][CH2:17][CH2:16]1)[CH2:5][CH2:6][N:7]2[CH2:12][C:13]([NH2:15])=O.CSC.B>O1CCCC1>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1([CH2:16][CH2:17][CH2:18]1)[CH2:5][CH2:6][N:7]2[CH2:12][CH2:13][NH2:15]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 86712761HCID 86712761, compound

Product 1

HCID 86712760HCID 86712760, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 40 mg (0.16 mmol) of 2-(5′-fluoro-2′,3′-dihydro-1′H-spiro[cyclobutane-1,4′-quinolin]-1′-yl)-acetamide obtained in step 31.4 in 1 ml of tetrahydrofurane was treated with 38 μl (0.40 mmol) of borane dimethylsulfide and heated to 70° C. for two hours. The mixture was quenched with water and hydrochloric acid, diluted with dichloromethane and extracted twice with water. The combined aqueous phases were set to pH 10 with sodium hydroxide solution and extracted 3× with dichloromethane. The combined organic phases were dried and evaporated to yield 10 mg of the title compound as an oil.

Workup

  1. customThe mixture was quenched with water and hydrochloric acid
  2. additiondiluted with dichloromethane
  3. extractionextracted twice with water
  4. extractionextracted 3× with dichloromethane
  5. customThe combined organic phases were dried
  6. customevaporated

Sources & evidence

ORD record
ord-2e4c8cc91e9d460490ab327c1a6f734c
Source dataset
uspto-grants-2015_10
Patent number
US09169253B2

Reaction notes

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