Hydrochloric Acid → HCID 67440879, compound

HRID 1255699Notes

Reaction equation

HRID 1255699 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][NH:11][C:12]1[N:19]=[C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]([B:27]3[O:31]C(C)(C)C(C)(C)O3)=[C:23]([CH:36]=[O:37])[CH:22]=2)[CH:17]=[CH:16][C:13]=1[C:14]#[N:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[CH2:1]([O:8][CH2:9][CH2:10][NH:11][C:12]1[N:19]=[C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]3[B:27]([OH:31])[O:37][CH2:36][C:23]=3[CH:22]=2)[CH:17]=[CH:16][C:13]=1[C:14]#[N:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86636442HCID 86636442, compound

Product 1

HCID 67440879HCID 67440879, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear solution of 2-(2-benzyloxy-ethylamino)-6-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-nicotinonitrile (7, 9 g, 18 mmol) in MeOH (anhydrous, 200 mL) was slowly added NaBH4 (4.11 g, 108 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. The solid formed was filtered, washed with water and air-dried to give 3.3 g (45.6% yield) of the title compound as a white solid.

Workup

  1. customThen the solution was slowly evaporated in vacuo
  2. customThe solid formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-ee3ece75c6ac4f6597537e4b7113aaae
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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