Diisopropylethylamine → HCID 58707278, compound

HRID 2426050Notes

Reaction equation

HRID 2426050 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([NH2:11])[CH2:3][CH2:2]1.F[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[S:20]([CH3:23])(=[O:22])=[O:21].C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[F:19][C:17]1[CH:18]=[CH:13][C:14]([S:20]([CH3:23])(=[O:22])=[O:21])=[C:15]([NH:11][CH:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[O:1][CH2:2][CH2:3]2)[CH:16]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27583362,4-Difluoro-1-(methylsulfonyl)benzeneHCID 49619573,4-Dihydro-2H-1-benzopyran-4-amine

Product 1

HCID 58707278HCID 58707278, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of chroman-4-amine (0.38 g, 2.55 mmol), 2,4-difluoro-1-(methylsulfonyl)benzene (0.49 g, 2.55 mmol) and diisopropylethylamine (2.2 mL, 12.74 mmol) in N,N-dimethylformamide (10 mL) was stirred at 90° C. for 16 h. The reaction mixture was diluted with water and extracted with diethyl ether. The combined extracts were washed with water and brine, dried, and concentrated under reduced pressure to yield 0.48 g of a yellow oil. The residue was purified by PTLC (25% ethyl acetate in hexanes) to give 0.45 g (55%) of the desired aniline: 1H NMR (400 MHz, CDCl3) δ 7.62 (dd, 1H), 7.35 (d, 1H), 7.28 (m, 1H), 6.91 (m, 1H), 6.85 (d, 1H), 6.57 (dd, 1H), 6.42 (dd, 1H), 4.49 (m, 1H), 4.34 (bs s, 1H), 4.29 (m, 2H), 2.86 (s, 3H), 2.23 (m, 2H). MS (ESI) m/z: Calculated: 321.08; Observed: 322.2 (M++1).

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined extracts were washed with water and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02d22453275043848862b264d41e4b80
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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