Pyridine → HCID 67287330, compound

HRID 1626464Notes

Reaction equation

HRID 1626464 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(Cl)(=O)C(Cl)=O.[Br:33][C:34]1[CH:35]=[CH:36][C:37]([NH2:40])=[N:38][CH:39]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C>[Br:33][C:34]1[CH:35]=[CH:36][C:37]([NH:40][C:17]([C:16]2[CH:15]=[CH:14][C:13]([O:12][C:11]3[CH:10]=[C:9]4[C:4]([CH:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:6][CH2:7][O:8]4)=[CH:3][C:2]=3[Cl:1])=[CH:21][CH:20]=2)=[O:19])=[N:38][CH:39]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 706222-Amino-5-bromopyridineHCID 582443954-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

Product 1

HCID 67287330HCID 67287330, compoundYield 69.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation B; 460 mg, 1.22 mmol) was diluted with DCM (5 mL) followed by the addition of oxalyl chloride in DCM (2M) (671 μL, 1.34 mmol) and DMF (1 drop). 5-Bromopyridin-2-amine (634 mg, 3.66 mmol) and pyridine (966 mg, 12.2 mmol) were added and the reaction was stirred at ambient temperature for 2 hours. The reaction was diluted with ethyl acetate and washed with 2N HCl, water, dried over MgSO4, filtered and concentrated. The material was purified on silica gel eluting with 5% ethyl acetate/hexanes to 70% ethyl acetate/hexanes to yield the desired compound (450 mg, 0.846 mmol, 69.3% yield).

Workup

  1. washwashed with 2N HCl, water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe material was purified on silica gel eluting with 5% ethyl acetate/hexanes to 70% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1acbc6f532114701ad7c934c2329e4bb
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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