Triethylamine → 5-bromo-N,N-dimethylpicolinamide

HRID 1177133노트

반응식

HRID 1177133 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.Cl.[CH3:12][NH:13][CH3:14].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:12][N:13]([CH3:14])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:10]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 6085445-Bromopyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 228316185-bromo-N,N-dimethylpicolinamide수율 46%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-bromopyridine-2-carboxylic acid (3.00 g, 14.85 mmol), dimethyl amine hydrochloride (1.82 g, 22.30 mmol) and triethylamine (6.21 ml, 44.60 mmol) in 20 mL of DMF was added HATU (8.47 g, 22.30 mmol). The mixture was stirred at room temperature overnight, quenched with water, extracted with 3×EtOAc. The combined organic layer was washed with 2×H2O, dried with Na2SO4, concentrated and purified by Biotage column chromatography with 60-70% EtOAc in hexanes to give a yellow oil (1.56 g, 46% yield). 1H NMR (400 MHz, CDCl3) δ 8.59 (d, J=1.77 Hz, 1 H) 7.88 (dd, J=8.34, 2.27 Hz, 1 H) 7.52 (d, J=8.34 Hz, 1 H) 3.06 (d, J=14.15 Hz, 6 H); LCMS for C8H9BrN2O m/z 229.00 (M+H+).

후처리

  1. customquenched with water
  2. extractionextracted with 3×EtOAc
  3. washThe combined organic layer was washed with 2×H2O
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. custompurified by Biotage column chromatography with 60-70% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-786d88f1af86493aa952fb2722aaa09b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

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