Hydrochloric Acid → HCID 67440879, compound

HRID 1483707Notes

Reaction equation

HRID 1483707 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-c4c2d2c6990f4d1a99ca38ac8fb47ec3
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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