Triethylamine → 4-Bromoquinoline-2-carboxylic acid

HRID 1497324Notes

Reaction equation

HRID 1497324 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=[O:13])[CH:3]=1.[NH2:15][C@@H:16]1[C@@H:21]([OH:22])[CH2:20][CH2:19][O:18][CH2:17]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=[O:13])[CH:3]=1.[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:15][C@@H:16]2[C@@H:21]([OH:22])[CH2:20][CH2:19][O:18][CH2:17]2)=[O:14])[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 155308124-Bromoquinoline-2-carboxylic acidHCID 55285677(3S,4S)-3-Aminotetrahydro-2H-pyran-4-OL

Product 2

HCID 155308124-Bromoquinoline-2-carboxylic acidHCID 602099044-bromo-N-[(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]quinoline-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Bromoquinoline-2-carboxylic acid (A3) was prepared as described in Example 1. To a solution of A3 (0.35 g, 1.4 mmol) in 6.0 mL CH2Cl2 was added (3S,4S)-3-aminotetrahydro-2H-pyran-4-ol (0.20 g, 1.7 mmol), BOP reagent (0.74 g, 1.7 mmol), and triethylamine (0.58 mL, 4.2 mmol). The reaction mixture was stirred at room temperature for 16 h, diluted with CH2Cl2, washed with water, dried over sodium sulfate, filtered, and concentrated. The resultant residue was subjected to silica gel chromatography eluting with 25-100% ethyl acetate in hexanes to afford 4-bromo-N-[(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]quinoline-2-carboxamide that gave a mass ion (ES+) of 353.1 (81Br) for M+H+.

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluting with 25-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-43e1082865624560852b0899dbf4a344
Source dataset
uspto-grants-2015_12
Patent number
US09199939B2

Reaction notes

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