Dimethylamine → 2-(5-bromopyridin-3-yl)-N,N-dimethylacetamide

HRID 712651Notes

Reaction equation

HRID 712651 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[N:6][CH:7]=1.[CH3:12][NH:13][CH3:14].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(N=C=NCCCN(C)C)C>CN(C=O)C.C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([N:13]([CH3:14])[CH3:12])=[O:11])[CH:5]=[N:6][CH:7]=1

Participants

9

Reactant 5

HCID 674DimethylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Product 1

HCID 537850792-(5-bromopyridin-3-yl)-N,N-dimethylacetamideYield 79.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(5-Bromo-pyridin-3-yl)-acetic acid (200 mg, 0.93 mmol), 2.0 M dimethylamine solution (0.93 mL, 1.9 mmol), HOBt (25 mg, 0.19 mmol) and triethylamine (0.38 mL, 2.8 mmol) are dissolved in 5.0 mL of DMF. Then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (290 mg, 1.9 mmol) is added. The reaction mixture is stirred for 16 hrs before 30 mL of water and 30 mL of DCM are added. The aqueous layer is separated and extracted with DCM (4×10 mL). The organic layers are combined, dried and concentrated to give the crude product which is purified by flash chromatography to give 180 mg of 2-(5-bromo-pyridin-3-yl)-N,N-dimethyl-acetamide.

Workup

  1. additionare added
  2. customThe aqueous layer is separated
  3. extractionextracted with DCM (4×10 mL)
  4. customdried
  5. concentrationconcentrated
  6. customto give the crude product which
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-d51482cd99d744c6aff3a515b1a1aa39
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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