Sodium borohydride → HCID 86636460, compound

HRID 1483741Notes

Reaction equation

HRID 1483741 reaction equation
[BH4-].[Na+].[F:3][CH:4]([F:33])[CH2:5][O:6][C:7]1[N:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([B:22]3[O:26]C(C)(C)C(C)(C)[O:23]3)=[C:18]([CH:31]=O)[CH:17]=2)[CH:12]=[CH:11][C:8]=1[C:9]#[N:10]>CO.C(Cl)Cl>[F:33][CH:4]([F:3])[CH2:5][O:6][C:7]1[N:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]3[B:22]([OH:26])[O:23][CH2:31][C:18]=3[CH:17]=2)[CH:12]=[CH:11][C:8]=1[C:9]#[N:10]

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86636461HCID 86636461, compound

Product 1

HCID 86636460HCID 86636460, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of NaBH4 (0.100 g, 2.6 mmol) in anhydrous methanol (20 mL) was added to a solution of 2-(2,2-difluoro-ethoxy)-6-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-nicotinonitrile (5.20 g, 12.1 mmol) in CH2Cl2 (80 mL) and stirred at room temperature for 5 minutes. Solid NaBH4 (0.815 g, 21.5 mmol) was then added portionwise over 30 minutes to the reaction at room temperature and the reaction stirred for an additional 30 minutes. The reaction was quenched by the addition of 60% aqueous acetic acid (5 mL), stirred for 30 minutes at room temperature then concentrated in vacuo. The residue was purified by silica gel flash column chromatography (AcOH/MeOH/CH2Cl2 1:1:100 v/v/v) to give the title compound as a viscous oil which was lyophilized to give a white solid (1.92 g, 48% yield).

Workup

  1. stirringthe reaction stirred for an additional 30 minutes
  2. customThe reaction was quenched by the addition of 60% aqueous acetic acid (5 mL)
  3. stirringstirred for 30 minutes at room temperature
  4. concentrationthen concentrated in vacuo
  5. customThe residue was purified by silica gel flash column chromatography (AcOH/MeOH/CH2Cl2 1:1:100 v/v/v)

Sources & evidence

ORD record
ord-61fc3aaf738648909a6a20de99c11dd6
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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