Triethylamine → HCID 66798963, compound

HRID 1193283Notes

Reaction equation

HRID 1193283 reaction equation
CO[C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11]Br.C(N(CC)CC)C.[NH2:21][C@H:22]1[C:31]2[C:26](=[CH:27][C:28]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:30]=2)[O:25][CH2:24][CH2:23]1>C1(C)C=CC=CC=1.O.ClCCl>[Cl:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:3](=[O:13])[N:21]([C@H:22]1[C:31]3[C:26](=[CH:27][C:28]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:30]=3)[O:25][CH2:24][CH2:23]1)[CH2:11]2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 22935208Methyl 2-(bromomethyl)-6-chlorobenzoateHCID 66799167HCID 66799167, compound

Product 1

HCID 66798963HCID 66798963, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

2-Bromomethyl-6-chlorobenzoic acid methyl ester (1.689 mmol, 1.0 eq) was dissolved in toluene (5.2 ml) and triethylamine (2.534 mmol, 1.5 eq), and (R)-methyl 4-aminochromane-7-carboxylate (A-04) (1.689 mmol, 1 eq) was added. The reaction mixture was refluxed for 16 h and then diluted with water and dichloromethane. The phases were separated and the aqueous phase was extracted with dichloromethane (2×). The organic phases were washed with sat. NaCl solution, dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, cyclohexane:EA 3:1), and the desired product (R)-methyl 4-(7-chloro-1-oxoisoindolin-2-yl)chromane-7-carboxylate (D-03) was thus obtained. Yield: 60%

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (2×)
  4. washThe organic phases were washed with sat. NaCl solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (silica gel, cyclohexane:EA 3:1)

Sources & evidence

ORD record
ord-1316cea81d4e4226ba193fedd2f09ff5
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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