Hydrochloric Acid → HCID 67439335, compound

HRID 1664438Notes

Reaction equation

HRID 1664438 reaction equation
[C:1]([NH:5][C:6]1[N:13]=[C:12]([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:11]=[CH:10][C:7]=1[C:8]#[N:9])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl>CN(C=O)C>[C:1]([NH:5][C:6]1[N:13]=[C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]3[B:21]([OH:25])[O:22][CH2:23][C:17]=3[CH:16]=2)[CH:11]=[CH:10][C:7]=1[C:8]#[N:9])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86636466HCID 86636466, compound

Product 1

HCID 67439335HCID 67439335, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-tert-butylamino-6-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-nicotinonitrile (7, 1 g, 2.38 mmol) in DMF (anhydrous, 100 mL) was added NaBH4 (0.55 g, 14.25 mmol). The reaction was kept at r.t. for 4 h, before the addition of HCl (1 M, 30 mL). The reaction was kept O/N. All the volatile components were removed in vacuo. Purification was accomplished by preparative HPLC, eluting with 5%-80% ACN/water gradient, to afford 430 mg (56% yield) of the title compound as a white solid.

Workup

  1. customAll the volatile components were removed in vacuo
  2. customPurification
  3. washeluting with 5%-80% ACN/water gradient

Sources & evidence

ORD record
ord-c1b08a9a8f9b4d5caef0ae8babd137d1
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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