Sodium borohydride → HCID 178436715, compound

HRID 1192519Notes

Reaction equation

HRID 1192519 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[CH:9])=[C:6](/[N:10]=[N:11]/[N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)=[C:4]([C:24](=[O:26])[CH3:25])[CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[C:7]([C:8]#[CH:9])=[C:6](/[N:10]=[N:11]/[N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)=[C:4]([CH:24]([OH:26])[CH3:25])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178436714HCID 178436714, compound

Product 1

HCID 178436715HCID 178436715, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-{4-chloro-6-[(1E)-3,3-diethyltriaz-1-en-1-yl]-5-ethynyl-3′-fluorobiphenyl-2-yl}ethanone (2.3 g, 6.1 mmol) in methanol (38 mL) at 0° C. was treated with sodium borohydride (0.46 g, 12 mmol) in two portions and stirred at 0° C. for 30 minutes. The reaction mixture was quenched with water at 0° C., poured into saturated sodium bicarbonate (50 mL), and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine (50 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product (quantitative). This material was used without further purification. LCMS for C20H22ClFN3O (M+H)+: m/z=374.1; Found: 373.9.

Workup

  1. customThe reaction mixture was quenched with water at 0° C.
  2. additionpoured into saturated sodium bicarbonate (50 mL)
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe combined organic extracts were washed with brine (50 mL)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-afd7184ef69c432e83c55765ca5f9621
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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