Hydrochloric Acid → HCID 67440879, compound

HRID 1471556Notes

Reaction equation

HRID 1471556 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-ab38bb8086aa4ad092273715103e69ff
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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