Methanol → HCID 18518173, compound

HRID 1843943Notes

Reaction equation

HRID 1843943 reaction equation
S1C=CC=C1.[F:6][C:7]1[CH:18]=[CH:17][C:10]2[S:11][CH:12]=[C:13]([CH2:14][C:15]#[N:16])[C:9]=2[CH:8]=1.CO>N.C(Cl)(Cl)Cl.[Ni]>[F:6][C:7]1[CH:18]=[CH:17][C:10]2[S:11][CH:12]=[C:13]([CH2:14][CH2:15][NH2:16])[C:9]=2[CH:8]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 8030ThiopheneHCID 18518168HCID 18518168, compound

Product 1

HCID 18518173HCID 18518173, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

Methanolic ammonia solution (15 mL) and thiophene solution (1 mL) were added to Raney Ni (5 g) taken in a reaction flask. This was followed by the addition of (5-Fluoro-benzo[b]thiophen-3-yl)-acetonitrile (I-45b: 700 mg, 3.66 mmol) in methanolic ammonia solution (15 mL) at 0° C. The resulting reaction mass was stirred at 10° C. overnight under hydrogen atmosphere. The reaction was monitored by TLC (5% methanol in chloroform). The reaction mass was filtered, washed with methanol and the filtrate was concentrated under reduced pressure to afford 500 mg of the crude product which was used for the next step without further purification. LCMS: 92.76%, m/z=196.1 (M+1)

Workup

  1. customtaken in a reaction flask
  2. customThe resulting reaction mass
  3. filtrationThe reaction mass was filtered
  4. washwashed with methanol
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49015bdd763449a39622cd53d6111ee0
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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