Diisopropylethylamine → HCID 59408770, compound

HRID 1188132Notes

Reaction equation

HRID 1188132 reaction equation
CC[N:3](C(C)C)C(C)C.[I-].ClC1C=CC=C[N+]=1C.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:30]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[N:29]=[C:28]([C:37]([OH:39])=O)[CH:27]=2)=[CH:22][CH:21]=1.[Br:40][C:41]1[CH:49]=[CH:48][C:44](C(O)=O)=[CH:43][N:42]=1>C1COCC1>[Br:40][C:41]1[N:42]=[C:43]([NH:3][C:37]([C:28]2[CH:27]=[C:26]([C:23]3[CH:22]=[CH:21][C:20]([F:19])=[CH:25][CH:24]=3)[N:30]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[N:29]=2)=[O:39])[CH:44]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 2389326-Bromonicotinic acidHCID 59408741HCID 59408741, compound

Product 1

HCID 59408770HCID 59408770, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIPEA (5.5 ml, 29 mmol) and 2-chloro-1-methylpyridinium iodide (8 g, 26 mmol) were added to a solution of 5-bromopyridin-2-amine 1 (2.56 g, 14.8 mmol) and 6-bromonicotinic acid (3 g, 14.8 mmol) 2 in THF (150 ml). The reaction mixture was stirred at RT for 4 days. Then the precipitate was filtered off. The filtrate was concentrated and dissolved in chloroform (250 ml), washed with water and brine and dried over Na2SO4. The solvent was evaporated to give a crude product, which was recrystallized from ethyl acetate to give 6-bromo-N-(5-bromopyridin-2-yl)nicotinamide 3 (4.3 g, 81%) as a white solid. Mp. 204-205° C.

Workup

  1. filtrationThen the precipitate was filtered off
  2. concentrationThe filtrate was concentrated
  3. dissolutiondissolved in chloroform (250 ml)
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated
  7. customto give a crude product, which
  8. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ce22f6db93b74b3f9e7ea271aebb7381
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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