Hydrochloric Acid → HCID 67439874, compound

HRID 1664366Notes

Reaction equation

HRID 1664366 reaction equation
C([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[B:24]1[O:28]C(C)(C)[C:26](C)(C)[O:25]1)[O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([N:15]([CH2:17][CH2:18][O:19][CH3:20])[CH3:16])[N:8]=1)=O.[BH4-].[Na+].Cl>CO>[OH:28][B:24]1[C:23]2[CH:22]=[CH:21][C:5]([O:6][C:7]3[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([N:15]([CH2:17][CH2:18][O:19][CH3:20])[CH3:16])[N:8]=3)=[CH:4][C:3]=2[CH2:26][O:25]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86636426HCID 86636426, compound

Product 1

HCID 67439874HCID 67439874, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear solution of 6-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-2-[(2-methoxy-ethyl)-methyl-amino]-nicotinonitrile (7) (15 g, 343 mmol) in MeOH (anhydrous, 300 mL) was slowly added NaBH4 (7.83 g, 206 mmol). The reaction was stirred at room temperature 4 hours, before the addition of HCl solution (1 M, 200 mL). The stirring was kept at room temperature overnight. Then the solution was slowly evaporated in vacuo. Purification was accomplished by reverse phase Biotage with 10%-100% MeOH/H2O gradient to afford 3 g (26% yield) of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.74 (d, J=8.6 Hz, 1H), 7.70 (d, J=8.2 Hz, 1H), 7.13-7.09 (m, 2H), 6.23 (d, J=8.2 Hz, 1H), 5.08 (s, 2H), 4.78 (s, 1H), 3.56 (t, J=5.7 Hz, 2H), 3.36 (t, J=5.7 Hz, 2H), 3.27 (s, 3H), 3.23 (s, 3H); ES-MS: m/z 340 (M+H)+; HPLC: 99.38% (220 nm), 98.71% (MaxPlot).

Workup

  1. customThen the solution was slowly evaporated in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-e7930d4233f345cb81a6a46f091050d9
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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