Sodium borohydride → HCID 57969220, compound

HRID 1483704Notes

Reaction equation

HRID 1483704 reaction equation
[BH4-].[Na+].C([C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][C:22]=1[B:23]1[O:27][C:26](C)(C)C(C)(C)[O:24]1)[O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[C:11]([O:18][CH3:19])[N:10]=1)=O>CO.C(Cl)Cl>[OH:24][B:23]1[C:22]2[CH:21]=[CH:20][C:7]([O:8][C:9]3[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[C:11]([O:18][CH3:19])[N:10]=3)=[CH:6][C:5]=2[CH2:26][O:27]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 57968972HCID 57968972, compound

Product 1

HCID 57969220HCID 57969220, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of NaBH4 (0.077 g, 2.0 mmol) in anhydrous methanol (10 mL) was added to a solution of 6-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-2-methoxy-nicotinamide (2.51 g, 6.30 mmol) in CH2Cl2 (40 mL) and stirred at room temperature for 5 minutes. Solid NaBH4 (0.400 g, 10.6 mmol) was then added portionwise over 45 minutes at room temperature. The reaction was stirred for an additional 30 minutes then quenched by the addition of 50% aqueous acetic acid (1 mL). After stirring for an additional 30 minutes at room temperature, the solution was concentrated in vacuo. The residue was purified by silica gel flash column chromatography (AcOH/MeOH/CH2Cl2 1:3:100 v/v/v) to give the title compound as a white fluffy solid (0.220 g, 12% yield).

Workup

  1. stirringThe reaction was stirred for an additional 30 minutes
  2. customthen quenched by the addition of 50% aqueous acetic acid (1 mL)
  3. stirringAfter stirring for an additional 30 minutes at room temperature
  4. concentrationthe solution was concentrated in vacuo
  5. customThe residue was purified by silica gel flash column chromatography (AcOH/MeOH/CH2Cl2 1:3:100 v/v/v)

Sources & evidence

ORD record
ord-18e7365029c2464ba4f97f123384471f
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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