Sodium borohydride → HCID 67440957, compound

HRID 1255717Notes

Reaction equation

HRID 1255717 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]1[C:11]([C:12]#[N:13])=[CH:10][N:9]=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([B:21]3[O:25]C(C)(C)[C:23](C)(C)[O:22]3)=[C:17](C=O)[CH:16]=2)[CH:7]=1)[CH3:4]>CO.C(Cl)Cl>[CH2:3]([O:5][C:6]1[C:11]([C:12]#[N:13])=[CH:10][N:9]=[C:8]([O:14][C:15]2[CH:16]=[CH:17][C:18]3[B:21]([OH:25])[O:22][CH2:23][C:19]=3[CH:20]=2)[CH:7]=1)[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86636452HCID 86636452, compound

Product 1

HCID 67440957HCID 67440957, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of NaBH4 (0.10 g, 2.6 mmol) in anhydrous methanol (20 mL) was added to a solution of 4-ethoxy-6-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-nicotinonitrile (3.53 g, 8.95 mmol) in CH2Cl2 (80 mL) and stirred at room temperature for 5 minutes. Solid NaBH4 (0.58 g, 15.3 mmol) was then added portionwise over 30 minutes at room temperature. The reaction mixture was stirred for an additional 30 minutes, quenched by the addition 70% aqueous acetic acid (3 mL) then stirred for an additional 1 hour at room temperature. The reaction was concentrated and the residue 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. The oil was lyophilized to give a white solid (0.781 g, 29% yield).

Workup

  1. stirringThe reaction mixture was stirred for an additional 30 minutes
  2. customquenched by the addition 70% aqueous acetic acid (3 mL)
  3. stirringthen stirred for an additional 1 hour at room temperature
  4. concentrationThe reaction was concentrated
  5. customthe residue purified by silica gel flash column chromatography (AcOH/MeOH/CH2Cl2 1:1:100 v/v/v)

Sources & evidence

ORD record
ord-1041765564244fb18a6776ebd0b27fbe
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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