Hydrochloric Acid → HCID 57969026, compound

HRID 1483681Notes

Reaction equation

HRID 1483681 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH3:36])[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([O:18][C:19]2[CH:24]=[CH:23][C:22]([B:25]3[O:29][C:28](C)(C)C(C)(C)[O:26]3)=[C:21](C=O)[CH:20]=2)[N:11]=1)(C)(C)C.[BH4-].[Na+].Cl>CO>[OH:26][B:25]1[C:22]2[CH:23]=[CH:24][C:19]([O:18][C:12]3[N:11]=[C:10]([N:9]([CH2:8][CH2:7][OH:6])[CH3:36])[CH:17]=[CH:16][C:13]=3[C:14]#[N:15])=[CH:20][C:21]=2[CH2:28][O:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57969223HCID 57969223, compound

Product 1

HCID 57969026HCID 57969026, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear solution of 6-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-2-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-nicotinonitrile (11) (485 mg, 0.903 mmol) in MeOH (anhydrous, 100 mL) was slowly added NaBH4 (101 mg, 2.65 mmol). The reaction was stirred at room temperature for 4 hours, before the addition of HCl solution (1 M, 60 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 51 mg (13.8% yield) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.22 (s, 1H), 7.92 (d, J=8.6 Hz, 1H), 7.75 (d, J=8.2 Hz, 1H), 7.24 (s, 1H), 7.16 (dd, J=7.8, 2.0 Hz, 1H), 6.43 (br. s., 1H), 4.98 (s, 2H), 3.90 (br. s., 1H), 3.47 (br. s., 2H), 3.39 (s, 2H, masked), 2.95 (br. s., 3H); HPLC: 98.18% (220 nm), 99.15% (254 nm), 99.16 (MaxPlot).

Workup

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

Sources & evidence

ORD record
ord-7bb976a179214eaf84fcbecca49f63e5
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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