Hydrochloric Acid → HCID 42643949, compound

HRID 1483754Notes

Reaction equation

HRID 1483754 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][NH:9][C:10]1[N:17]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([B:25]3[O:29]C(C)(C)[C:27](C)(C)[O:26]3)=[C:21](C=O)[CH:20]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13])(C)(C)C.[BH4-].[Na+].Cl>CO>[OH:29][B:25]1[C:22]2[CH:21]=[CH:20][C:19]([O:18][C:16]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([NH:9][CH2:8][CH2:7][OH:6])[N:17]=3)=[CH:24][C:23]=2[CH2:27][O:26]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86636470HCID 86636470, compound

Product 1

HCID 42643949HCID 42643949, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethylamino]-6-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-nicotinonitrile (7, 1.11 g, 2.12 mmol) in MeOH (anhydrous, 60 mL) was added NaBH4 (0.48 g, 12.7 mmol). The reaction was stirred at r.t for 4 h, before the addition of HCl (1 M, 20 mL). After overnight stirring, all volatile components were removed. Purification was accomplished by preparative HPLC, eluting with 5%-90% ACN/water gradient, to afford 86.3 mg (13% yield) of the title compound as a white solid.

Workup

  1. customall volatile components were removed
  2. customPurification
  3. washeluting with 5%-90% ACN/water gradient

Sources & evidence

ORD record
ord-58ab41065bae4a1a9af0a70694e9558c
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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