Acetic Acid → HCID 86729197, compound

HRID 868825Notes

Reaction equation

HRID 868825 reaction equation
[C:1](O)(=[O:3])[CH3:2].C(N(CC)CC)C.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][O:19][C:20]2[CH:27]=[CH:26][C:25]([B:28]3[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]3)=[CH:24][C:21]=2[C:22]#[N:23])[CH2:14][CH2:13]1>ClCCl>[C:1]([N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][O:19][C:20]2[CH:27]=[CH:26][C:25]([B:28]3[O:32][C:31]([CH3:34])([CH3:33])[C:30]([CH3:36])([CH3:35])[O:29]3)=[CH:24][C:21]=2[C:22]#[N:23])[CH2:14][CH2:13]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 86729195HCID 86729195, compound

Product 1

HCID 86729197HCID 86729197, compoundYield 134.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Glacial acetic acid (2.1 g, 0.035 mol), triethylamine (3.5 g, 0.035 mol) and 1-propanephosphonic anhydride (60% w/w in ethyl acetate) (11 ml, 0.0174 mol) are added to a solution of 2-(piperidin-4-ylmethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (4.0 g, 0.0116 mol) in dichloromethane (40 ml) at 0° C. under nitrogen. The reaction is stirred at room temperature for 15 h. The solution is evaporated and poured into water (200 ml). The mixture is extracted with dichloromethane (100 ml×2) and evaporated in a rotary evaporator. The crude product is purified by chromatography, giving 6.0 g of the desired product as colourless oil;

Workup

  1. customThe solution is evaporated
  2. additionpoured into water (200 ml)
  3. extractionThe mixture is extracted with dichloromethane (100 ml×2)
  4. customevaporated in a rotary evaporator
  5. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-807eaea6503c4d50be74bc0b3254f39c
Source dataset
uspto-grants-2015_03
Patent number
US08969335B2

Reaction notes

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