Sodium borohydride → HCID 178436715, compound

HRID 515849Notes

Reaction equation

HRID 515849 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-587a5c64997c43d8a4c59a6c8aa72a59
Source dataset
uspto-grants-2015_08
Patent number
US09108984B2

Reaction notes

Loading…